JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
Jun Shi
A Survey of Papers with a Focus on Synthetic Organic Chemistry
Statistics for JACS 1984:
O
O O
Total Number of Papers:
2,215
Papers focused on synthesis: 224
Total synthesis papers:
52
Top Organic Chemistry Authors:
L. A. Paquette: 14
M. J. Dewar:
12
E. J. Corey:
9
B. M. Trost:
8
H. C. Brown:
7
J. K. Stille:
4
O
O
O
N
H
O
O
!"Cyclopiazonic Acid
O
O
OH
Nature Products discussed in part or full
O
HO
OH
(±) -Talaromycin B
MeO
O
HO
(±)-Verrucarol
OH
H
N
O
NH
(-)-Ptilocaulin
O
HO
OH
HO
HO
HO
(+)-Bicyclomycin
Pretazettine
O
(±)-Hibiscone C
NH2
N
O
O
NH
O
O
(±)-Dehydrocostus
Lactone
(±)-Saxitoxin
O MeO2C
NH
H
Me
N
Me
NH
HN
HO
HO
H O
OH
H
HN
(+)-Actinobolin
O
HN
MeO
N
O
NH
HN
NH2HCl
HO
O
O
O
Haemathidine
O
O
O
O
OH
OH HN
O
O
H
(±)-Isognidione
(±)-Gnididione
O
N H
H
OH
HO
H
O
H
O
O
O
HO
O
H
O
H
O CH3
O
O
OH
(+)-Phyllanthocin
O
(±)-Estafiatin
O H
N
O
O
O
O
H
H
N
N
O
n-C5H11
(±)-Poitediol
(+)-Coriamyrtin
Anhydrocannabisativene
(+)-Dihydrocompactin
1
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
NOC Approach to Spiroketals. A Total Synthesis of (±) -Talaromycin B
Alan P. Kozikoweski and James G. Scripko; J. Am. Chem. Soc. 1984, 106, 353-355
N
NaOCl, Et3N
O
O
+
O
O
OH
O
O
N
TBAF
O
Br
steps
HO
(±)-Verrucarol
N
O
O
OTHP
O
O
O
Cl
O
!
OTMS
O
1.NaBH4
2. 470ºC
HO
OH
O
1. I2, NaHCO3,
H2O
2. NaOH, H2O
3. CH2N2
4. TsOH
NH
CO2Me O
O
1. heat
2. NaOH
3. CH2N2
4. DHP,
5. NaOH
1. HCO2H,
HO
2. Me2C(OMe)2
+
3. DHP, H
4. LAH,
5. TsCl, PhSeSePh
6. BuLi, PMS-Cl PhSe
7. TsOH
NH
O
O
CO2H
O2CPh
OH
NPMS
O
O
OH
NaOMe
O
OTMS
O
O
O
O
OTMS
EtO2C
OH
MeO3C
MeO2C
NH
Cl
Ph
1. KMnO4, CH2N2
2. DBU
TsOH, !
OH
EtO2C
(±) -Talaromycin B
O
O
O
HO
OH
Me
1. 1N HCl
O 2.
A Tandem Cycloaddition-Ene Strategy for the Synthesis of (±)-Verrucarol
and (±)-4,11-Diepi-12,13-deoxyverrucarol
Barry M. Trost, Patrick G. McDougal and Kenneth J. Haller;
J. Am. Chem. Soc. 1984, 106, 353-355
Cl
O
O
Ph
HO
O
O
O
Stereocontrolled Total Synthesis of (+)-Actinobolin by an Intramolecular DielsAlder Reaction of a Chiral Z Diene Derived from L-Threonine
Masato Yoshiok, Hisao Nakai, and Masaji Ohno, J. Am. Chem. Soc. 1984, 106, 11331135
OH
Then, MeOH
Amberlyst 15
steps
O
H
H2, Raney Ni
HO
O
O
O
O
OTMS
O
Jun Shi
NHPMS
HO
O
bromine-dioxane
complex
PhSe
O
1. O3, Py
2. O3, MeOH
HO
DMS
3. HF
4. Ala, DCC
NH2HCl
OH HN
O
OH
O
(+)-Actinobolin
O
2
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
Total Synthesis of (-)-Ptilocaulin
William R. Roush and Alan E. Walts, J. Am. Chem. Soc, 1984, 106, 721-723
O
O
4 steps
O
1. LDA,
Cl
Stereocontrolled Total Synthesis of (±)!and (+)-Bicyclomycin: New CarbonCarbon Bond-Forming Reactions on Electrophilic Glycine Anhydride Derivatives
Robert M. Williams, Robert W. Armstrong, and Jen-Sen Dung
J. Am. Chem. Soc, 1984, 106, 5748-5750
TiCl4
allytrimethylsilane
N
O
o
P(OEt)3
2. 9-BBN CHO
3. Li, EtNH2,
t-BuOH
4. PCC
O
N
Ph
Jun Shi
S
1.NBS, CCl4
NBn
PhCH2NHOH
O
BnN
N
BnN
2. NaS(py)
O
O
NBn 1eq. AgOTf
S
O
O
S
NBn
BnN
OTMS
N
O
NH
1. Pd black
1. Zn, AcOH
2. Jone's reagent
NH
HN
2. GDMP
N
LAH
O
1eq. AgOTf
S
(-)-Ptilocaulin
NBn
BnN
Total Synthesis of (-)-Ptilocaulin
Barry B. Snider and William C. Faith, J. Am. Chem. Soc, 1984, 106, 1443-1445
O
CuBr(CH3)S
O
O
1. MsCl
NaBH3SePh
O
H2O2
OH
O
BnN
H
N 2. 1.5 eq n-BuLi,
Bn
HO
HO
2 eq HMPA
2eq (Me3N)3P,
O2
O
O
HCl
O
O
O
O
O
O
NH
Ph
O
NH
MgBr
O
HN
O
NH
BnN
O
guanidine
OH
H
n-BuLi
O
NBn
O
BnN
O
HO
CHO
O
O
O
(-)-Ptilocaulin
OH
NBn
H
Me
O
HN
O
1.TFAA
2. CAN
O
HO
HO
OH
O
NH
H
Me
HO
(+)-Bicyclomycin
3
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
Jun Shi
Total Synthesis of (+)-Phyllanthocin
D. R. Williams and Sing-Yuen Sit, J. Am. Chem. Soc., 1984, 106, 2949-2954
EtO2C
O
steps
O
H
H
S
O
S
Li
MEMCl
H
H
CO2Et
S
H3C
H3C
S
H
OTBDPS
OSitBuPh2
Heat
O
O
O
O
O
O
OMEM
H
OH
BnO
O
OH
OH
S
S
1. H2/Pd/C
OMEM 2. Jones,
OBn
O
O
CH3
O
2. H2CrO4
(±)-Isognidione
O
Total Syntheses of the Amaryllidaceae Alkaloids (±)-Haemanthidine and (±)Pretazettine
Stephen F. Martin and Steven Davidsen, J. Am. Chem. Soc., 1984, 106, 6431-6433
MeO2C
CH2N2
3. ZnBr
4. (CH3)2SOCH2
5. Cinnamoyl
chloride
O
H
O
1.HgCl2, HgO
OMEM
H
O
O
CH3
OTBDPS
HMPA, t-BuLi, then TBAF BnO
(±)-Gnididione
N
O
OH
O
O
O
O
H
H
O
CHPh
O CH3
1. n-BuLi
2.CHOCH2NMeCO2C3H5
3. Pivaloyl Chloride
4. HCl
N
(+)-Phyllanthocin
O
O
O
O
O
O
OCOtBu
CHO
CO2C3H5
Bis Heterannulation 7. Total Synthesis of (±)-Gnididione and (±)-Isognidione
Peter A. Jacobi and Harold G. Selnick, J. Am. Chem. Soc., 1984, 106, 3240-3245
O
MeO2C
1. 2eq LiCH2NC
2. NaH, MeI
3.HOCH2CH2OH, H+
4. PhN(Me)3+Br_
CO2Me 5. DBU, Heat
6. DIBAL
O
O
MgBr
N
1. PhNMe3Br3
2. DBU
3. Pd(PPh3)4
O
O
O
N
CO2C3H5
1. DIBAL, MeOH
2. Pt, O2
3. CH3CO2CHO
OCOtBu
OCOtBu
O
CHO
O
pyrrolidine
AcOH-MeOH
1. LiCCMe
2. Swern
3.
O
N
O
N
Me
4
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
O
O
O
O
O
OCOtBu
MeO
O
LiOH
OH
OH
MeI
MeOH
N
O
Et3N, #
O
H
H
O
N H
H
O
H
MeO
Haemathidine
O
N H
H
OH
N
CO2Et
H
O
O
OH
MeO
O
N
CO2Et
O
NaOMe, MeOH
CO2Et PhH
O
2.
N
O
N
CO2Et 1. Et3O+BF4-, Na2CO3, HOAc
OCOtBu
N
CHO
O
NAc
POCl3, heat
MeO
Jun Shi
O
N
H
N
Me
Pretazettine
N
H
!"Cyclopiazonic Acid
Total Synthesis of the Unique Mycotoxin !"Cyclopiazonic Acid (!CA): An Unusual
Dimethylzinc-Mediated Replacement of a Phenylthio Substituent by a Methyl Group
Intramolecular [2+2] Photocycliztions. 2. Total synthesis of (±)-Hibiscone C
and a Contrathermodynamic Raney Nickel Desulfuriztion Reaction
(Gmelofuran)
Alan P. Kozikowski and Michael N. Greco, J. Am. Chem. Soc., 1984, 106, 6873-6874
Emil R. Koft and Amos B. Smith, III J. Am. Chem. Soc., 1984, 106, 2115-2121
O
O
CHO
CO2Et
O
NHAc
N
Ts
N
H
O
1. DBU, BuOH
2. H2, Raney Ni
1. ClCO2Et, Et3N
2. HCl
3. MeSiI, HN(SiMe)2
PhSCl
SPh
O
O
NAc
O
H
O
+
H
O
O
TsOH, reflux
O
O
H
O3, Ph3P
CO2Et
HO
O
H
hv
NHAc
N
CO2Et
SPh
CO2Et
HO
CO2Et
steps
O
O
NHAc
Me2Zn, CHCl3
PhSH, Mg(OTf)2
N
CO2Et
N
CO2Et
(±)-Hibiscone C
5
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
Total Synthesis of (±)-Saxitoxin
Peter A. Jacobi, Michael J. Martinelli, and Solvenko Polanc
J. Am. Chem. Soc., 1984, 106, 5594-5598
H
H
N
HN
O
N
H
HN
BF3•Et2O
O
S
S
OH
H
N
O
N
H
Total Synthesis of (±)-Poitediol and (±)-4-Epipoitediol
Robert C. Gadwood, Renee M. Lett and Jane E. Wissinger
J. Am. Chem. Soc., 1984, 106, 3869-3870
CO2Me
H
N
Ph
Ph
N
O
O NaOMe
S
O
steps
Ph MeO
S
S
H
CH2OH
BH3•DMS
N
O
H
Ph
BF3•Et2O
O
OH
S
S
1. Pd, HCO2H
2. PhOCCl
N
H
OPh
N
S
(±)-Poitediol
Total Synthesis of Guaianolides: (±)-Dehydrocostus Lactone and (±)-Estafiatin
James H. Rigby and JoAnn Zbur Wilson, J. Am. Chem. Soc., 1984, 106, 8217-8224
S
CH2OH
NH
O
N
H
S
O
O
N
S
H
1. Ac2O/Py
O
S
N
EtO
2. Et3O+BF4KHCO3
N
H
S
N
S
SEt
1. NaBH4
2. TFA
O
EtCO2-NH4+
1. Li/CH2NH2, reflux
130°C
2. DIA, MEMCl
OMe
OMe
1. TMSCl, NaI
2. swern
1. m-CPBA
2. dilithioacetate
3. Ph3P=CH2
MEMO
MEMO
O
O
H
CH2OH
N
N
HN
N
H
S
N
S
1. NBS,
wet, CH3CN HN
NH 2. chlorosulfoyl
isocyanate
H
N
N
H
HO
H
O
O
NH2
NH
N
OH
BF3•Et2O
NH
(±)-Saxitoxin
O
3. BF3•Et2O
O
CH2OAc
N
OMe
O
MgBr
H
HO
steps
Na, NH3
S
H
N
O
2. PCC
3. LiMe2Cu, Me2S
S
N
O
N
N
H
CH2OH
H
N
LiCCH
then !
O
O
1. MeLi, -78°C
H
N
OH
MeO
N
N
H
NaBH4
MeOCHCO2Me
CH2OH
H
N
N
S
Jun Shi
LDA,
+NH =CH
2
2
O
O
O
mCBPA
O
O
O
O
(±)-Dehydrocostus
Lactone
O
O
(±)-Estafiatin
6
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
Stereocontrolled Total Synthesis of (-)-Picrotoxinin and (+)-Coriamyrtin via a
Common Isotwistane Intermediate
Kiyoyuki Yamada etc, J. Am. Chem. Soc., 1984, 106, 4547-4552
O
O
OH
1. mCPBA
2. DBU
O
O
CO2Me
O
HO
1. HO(CH2)2OH,
TsOH
O
2. LAH, TBDMS
3. PCC
4. MeI, NaH
O
LDA
O
MoO5
OMe HMPA
Py O
O
OTBDMS
1. PhSONMeCH2Li
2. Al(Hg)
3. Ph3P=CH2
HO
4. HCl
5. Na
Br
OMe 3. NBS, -78°C
Br
OH
O
Br
TBDPSO
O
O
O
O
O
I
(+)-Dihydrocompactin
O
Total Synthesis of Anhydrocannabisativene
Thomas R. Bailey, Ravi S. Garigipati, Judith A. Morton and Steven M. Weinreb
J. Am. Chem. Soc., 1984, 106,3240-3245
O
O
OH
O Methyl glyoxylate
H2N
O
Br
S
O
S
O
1. RuCl3, NaIO4
S
OH
Br
O
O 2. Zn
HO
steps
S
O
O
O
O
PhO2S
1. Me3SiCl, NaI
2.PhSO2-Amberlyst
26-A
3. (HSCH2)2CH2,
BF3•Et2O
OMe
Br
O
1. t-BuOK
2. mCPBA
TBDPSO
O
OMe
O
NBS, RT
Br
O
O
O
1. t-BuOK
2. NBS,H2o
O
+
Br
OTBDM
1. LHMDS
O SO Ph 2. CH2N2
2
3. Al(Hg)
4. NaOMe
1. (HOCH2)2
TsOH
2. LAH
OMe
OTBDMS
O
O
O
HO
CO2MeO
O
1. CSCl, Py
2. NaH, DME
O
CO2Me
O
1. MeLi
2. Pb(OAc)2
OMe 3. t-AmOK
O
O
SO2Ph
OH
1. aq. AcOH
2. Et2NH O
CO2Me
Total Synthesis of (+)-Dihydrocompactin
Yuh-Lin Yang, Sukumar Manna and J.R.Falck,
J. Am. Chem. Soc., 1984, 106, 4547-4552
O
HO
O
Jun Shi
O
(+)-Coriamyrtin
n-C5H11
O
O
O
CO2Me
OAc
HN
O Hunig's Base
CO2Me
H
N
O
O
O
n-C5H11
n-C5H11
7
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
H
1. NaOH, MeOH
2. (COCl)2,
3. CH2N2
4. Ag2O/MeOH
CO2Me
O 1. Ba(OH)2
N
H
!
O
2. SOCl2/MeOH
TBDMSCl
n-C5H11
CO2Me
H
NHTs 1. LiOH, MeOH
N
2. 4-aminobutanol
DMF
3. K2CO3, reflux
OTBDMS
n-C5H11
NH
Me
OTBDMS HO
1. Na/NH3
2. BF3•Et2O
Ts
N
3. Jones reagent
O
N
H
Ph
n-C5H11
O H
N
N
NHTs
Me
O
O
O
H
OH
Cytochalasan D
E. Vedejs, 4617
see groupmeeting
"Cytochalasan"
Me
OH
Me
OH
Me
O
O
n-C5H11
O
O
OH
Pumiliotoxin B
L. E. Overman, 4192
See groupmeeting
"Indolizidine"
O
OMe
O
OH
CH3
N
O
O
(±)"Asteltoxin
S. L. Schreiber, 4186
see Classics I, Chapter 20
OTBDMS
H
N
N
Me OH
HO
OAc
n-C5H11
O H
N
H
H
CO2Me
Jun Shi
O
(±)-Quadrone
S. D. Burke, 4558
see groupmeeting
"Quadrone"
COOH
(±)-Nanaomycin A
L. S. Liebeskind, 4181
Anhydrocannabisativene
OH
OH
OH
COOH
COOH
Other Total Syntheses Published In 1984 in JACS
AcO
CO2CH3
O
OAc
(±)-Clavulones
E. J. Corey, 3384
Logic: 303-304
5, 15-DiHETE
K. C. Nicolaou, 5734
O
n-C5H11
OH
Leukotriene B4
K. C. Nicolaou, 3548
OMe
O
O
O
O
O
Hybridalactone
E. J. Corey, 2735
Logic: 307-309
O
MeO
O
O
(±)"Avenaciolide
S. L. Schreiber, 7200
H
H
O
O
dl-Quassin
P. A. Grieco, 3539
8
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
Methodology
E. J. Corey:
Silane Chemistry:
A New Method for the synthesis of Organic Nitro Compounds
E. J. Corey, Bertil Samuelsson and Fredrick A. Luzzio
J. Am. Chem. Soc., 1984, 106, 3682-3683
N-Trimethylsilyl Imines: Applications to the Synthesis of !-Lactams
Deok-Chan Ha, David J. Hart and Teng-Kuei Yang
J. Am. Chem. Soc., 1984, 106, 4819-4825
OLi
1.
R
2. HCl, H2O
R
NH
O
DTBP
SiMe2
145°C
O
SiMe2
SiMe2
The Michael Reaction of Silyl Enol Ethers or Ketene Silyl Acetals with Conjugated
Nitro Olefins Acitivated by the Lewis Acid: New Synthesis of 1, 4-Diketones and
"#Keto Esters
Akira Yoshikoshi etc, J. Am. Chem. Soc., 1984, 106, 2149-2156
R
R
Lewis acid
+
O
R1
SiMe3
R2
R3
R1
Li
R2
OTMS
R3
R1
R2
RN
PR3
O
O
O
RNO2
+ R3P O
O
O
O
Rhodium(I)-Catalyzed Hydrogenation of Olefin. The Documentation of HydroxylDirected Stereochemical Control in Cyclic and Acyclic Systems
David A. Evans and Michael M. Morrissey
J. Am. Chem. Soc., 1984, 106, 3866-3868
OH
OH
O
OTMS
O3
D. A. Evans:
O
Application: ACIEE, 2007, 46(4), 541-544
H2
Base-Induced Rearrangement of 1-(Trimethylsilyl)allyic Alcohols. Stereo- and
Regioselective Synthesis of Silyl Enol Ethers through Lithium Homoenolates
Isao Kuwajima etc, J. Am. Chem. Soc., 1984, 106,1773-1778
OLi
PR3
Mn3O(OAc)7
CH3COOH
Rh(I)
NO2
OSi(CH3)3
RN
O
OH
Si
Me2
R
R$3P
New and General Synthesis of Polycyclic "-Lactone by Double Annulation
E. J. Corey and Myung-chol Kang
J. Am. Chem. Soc., 1984, 106, 5384-5385
Regiochemistry of Alkenylsilyl and Alkenyldisilanyl Radical Cyclizations
Thomas J. Barton and Anthony Revis
J. Am. Chem. Soc., 1984, 106, 3802-3805
SiMe2H
N3 +
R
OEt
NSiMe3
Jun Shi
OTMS
Li
alkylation
R3
R1
R2
OLI
R1
R2
TMS
R3
R4
Asymmetric Acylation Reactions of Chiral Imide Enolates. The First Direct
Approach to the Construction of Chiral !-Dicarbonyl Synthons
D. A. Evans, M. D. Ennis and T. Le, J. Am. Chem. Soc., 1984, 106, 3866-3868
O
R3
O
O
O
N
R1
R2COCl
O
O
N
O
R2
R1
9
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
J. K. Stille:
Palladium-catalyzed coupling of vinyl triflates with organostannanes. A short
synthesis of pleraplysillin-1
William J. Scott, G. T. Crisp, J. K. Stille
J. Am. Chem. Soc.; 1984; 106, 4630-4632.
Palladium-catalyzed cross-coupling of vinyl iodides with organostannanes:
synthesis of unsymmetrical divinyl ketones
W. F. Goure, Michael E. Wright, P. D. Davis, Sharada S. Labadie, J. K. Stille
J. Am. Chem. Soc.; 1984; 106; 6417-6422.
Asymmetric synthesis of quaternary carbon centers
A. I. Meyers, Michael Harre, Robert Garland
J. Am. Chem. Soc.; 1984; 106; 1146-1148.
O
Ph
Palladium-catalyzed cross coupling of allyl halides with organotin reagents: a method
of joining highly functionalized partners regioselectively and stereospecifically
Forrest K. Sheffy, J. P. Godschalx, J. K. Stille
J. Am. Chem. Soc.; 1984; 106; 4833-4840.
TMS
Me
OTf
1. Me3Sn
Pd(PPh3)4/CO/LiCl
Me
Me
Me
+
N
O Ph
H
LDA
N
R1X
H2N
OH
O
H
R1
O
LDA
R2X
H+
O Ph
N
Me
O
O
R1
R2
R1
Ph
COOH
H+
O
O
Ph
2. BF3•Et2O, 100°C
R2
R1
COOH
Me
Me
Me
O Ph
COOH
Palladium-catalyzed carbonylative coupling of vinyl triflates with organostannanes.
A total synthesis of (±)-!9(12)-capnellene
G. T. Crisp, William J. Scott, John K. Stille
J. Am. Chem. Soc.; 1984;106, 7500-7506
Me
Jun Shi
Capnellene
B. M. Trost:
A. I. Meyers:
Asymmetric addition to chiral naphthyloxazolines. A facile route to 1,1,2-trisubstituted
1,2-dihydronaphthalenes in high enantiomeric excess
Bruce A. Barner, A. I. Meyers
J. Am. Chem. Soc.; 1984; 106; 1865-1866.
Sulfones as chemical chameleons. Cyclization via 1,1-dipole synthons
Barry M. Trost, M. Reza Chadiri
J. Am. Chem. Soc.; 1984; 106, 7260-7261.
R1
PhSO2
OMe
Ph
C
R2
R1
H
C
R2
O
O
N
1. RLi
2. E+
E
E
R
CHO
R
H
H
OX
O
O
+
Br
SO2Ph
SO2Ph
10
JACS: 1984 Year in Review
Baran Group Meeting
3/28/2007
2-Alkoxybenzo-1,3-dithiole 1,1,3,3-tetraoxide. A carbonyl 1,1-dipole synthon
Barry M. Trost, Peter Quayle
J. Am. Chem. Soc.; 1984; 106, 2469-2471.
O
RO2S
O2S
R
3
R: a=Ph
b=PhCHCHc=PMB
O
SO2R
O
n
Br
[ML2]
TMS
O
C
R
MgCl
Jun Shi
TMS
TiCl4
SO2
n
Stereocontrolled 1,1,2-trialkylation of ketones
Barry M. Trost, Alberto Brandi
J. Am. Chem. Soc.; 1984; 106, 5041-5043
O
OTMS
Sulfoximine-directed osmylation: synthesis of enantiomerically pure
dihydroxycycloalkanones
Carl R. Johnson, Michael R. Barbachyn J. Am. Chem. Soc.; 1984; 106; 2459-2461.
R+
O
R
Herbert C. Brown
Hydroboration. 68. Chiral synthesis via organoboranes. 1. A simple procedure
to achieve products of essentially 100% optical purity in hydroboration of
alkenes with monoisopinocampheylborane. Synthesis of boronic esters and
derived products of very high enantiomeric purities
Herbert C. Brown, Bakthan Singaram
J. Am. Chem. Soc.; 1984; 106, 1797-1800
H
BH3
Li+
MeI, 0°C
H H
B
Ipc
Miscellaneous
Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II): an effective catalyst
for cross-coupling of secondary and primary alkyl Grignard and alkylzinc reagents
with organic halides
Tamio Hayashi, Mitsuo Konishi, Yuji Kobori, Makoto Kumada, Taiichi Higuchi, Ken Hirotsu
J. Am. Chem. Soc.; 1984; 106, 158-163
HO
O
PhS
PhS
NMe
O
HO
NMe HO
OH
O
O
SPh
SPh
O
NHMe
NMe
OH OH
Ring expansion and cleavage of succinoin derivatives. Geminal acylation,
reductive succinoylation, and stereoselective spiro annelation methods
Junichi Shimada, Koichi Hashimoto, Byeang Hyean Kim, Eiichi Nakamura, Isao
Kuwajima
J. Am. Chem. Soc.; 1984; 106, 1759-1773.
CO2Et
CO2Et
OTMS
R1
R2
O
O
R1
OTMS
R2
O
11