VI International School On Organometallic Chemistry
Marcial Moreno Mañas
Instruction for Authors: Title (12 pt with initial caps, centered, bold)
(one line blank)
Author(s)' Name(s), Senior Author,* Underline Speaker's Name (12pt, centered, normal text)
(one line blank)
Affiliation(s) (italic, 12 pt, centered)
e-mail address of the corresponding author (12pt, centered, normal text)
(one line blank)
Please read these instructions carefully and prepare your abstract using this template.
(1) The abstract should be written in English using 12 pt Times New Roman font or
equivalent, right-left justified, normal text, with single line spacing.
(2) Each structural formulas, tables, figures, and references should be integrated in the
text.
(3) The deadline for submission of the abstract is April 30th, 2013.
(4) The abstract should be sent as WORD files
Please name the word and PDF files: your family name-first name, such as
Chatani-N.doc or Chatani-N.docx
(5) Schemes and Figures: ACS style.
(6) References: ACS style.
See examples for Invited Speakers and for other oral or poster communications
For Invited Speakers (45 + 15 min lectures) a small biography and a photograph
must be provided. Example:
Naoto Chatani
Department of Applied Chemistry, Faculty of Engineering
Osaka University
Suita, Osaka 565-0871, Japan
Phone: +81-6879-7397, Fax: +81-6879-7396
E-mail: chatani@chem.eng.osaka-u.ac.jp
Naoto Chatani studied chemistry at Osaka University and received his Ph. D. in 1984
under the guidance by Profs. Noboru Sonoda and Shinji Murai. In 1984 he joined the
Institute of Scientific and Industrial Research at Osaka University and worked in the
laboratory of Prof. Terukiyo Hanafusa. After postdoctoral studies (1988-1989 under Prof.
Scott E. Denmark, the University of Illinois, Urbana-Champaign), he moved back to
Osaka University and worked with Prof. Shinji Murai as Assistant Professor. He was
promoted to Associate Professor in 1992 and Professor in 2003. His research interests
center on the area of catalysis. Awards:Young Chemist Award of the Chemical Society of
Japan (1991). The fourth Green and Sustainable Chemistry Award: Minister of Education,
Sports, Culture, Science and Technology Prize (2005).
Selected Reviews and Papers: (10.5pt)
1. “Ruthenium-Catalyzed Carbonylation at ortho C-H Bonds in Aromatic Amides Leading to
Phthalimides: C-H Bond Activation Utilizing a Bidentate System”; Inoue, S.; Shiota, H.; Fukumoto,
Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898.
2. “Skeletal Reorganization of Enynes through Electrophilic Activation of Alkynes with Various Metal
Catalysts: Double Cleavage of C-C Double Bond and Triple Bonds”; Lee, S. I.; Chatani, N. Chem.
Commun. (Feature Article) 2009, 371.
3. “Rhodium-Catalyzed Reductive Cleavage of Carbon-Cyano Bonds with Hydrosilanes: A Catalytic
Protocol for Removal of Cyano Groups”; Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am.
Chem. Soc. 2009, 131, 3174.
4. “Rhodium-Catalyzed Silylation and Intramolecular Arylation of Nitriles via the Silicon-Assisted
Cleavage of Carbon-Cyano Bonds”; Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc.
2008, 130, 15982.
5. “Brønsted Acid Catalyzed Formal Insertion of Isocyanides into a C-O Bond of Acetals”; Tobisu, M.;
Kitajima, A.; Yoshioka, S.; Hyodo, I.; Oshita, M.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 11431.
6. “Rh(I)-Catalyzed Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic
Acids Leading to Indenones”; Harada, Y.; Nakanishi, J.; Fujihara, H.; Tobisu, M.; Fukumoto, Y.;
Chatani, N. J. Am. Chem. Soc. 2007, 129, 5766.
For Short (12+3 min), FLASH (5 min) presentations and posters:
Stereoselective Synthesis of Tetrahydroisoquinolines and Tetrahydrobenzazepines
from Phthalan and Isochroman
Daniel García, Haythem K. Dema, Francisco Foubelo and Miguel Yus*
Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis
Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
foubelo@ua.es, yus@ua.es
Many tetrahydroisoquinoline1 and tetrahydrobenzazepine natural products are cytotoxic
agents that display a wide range of biological activities. For these reasons, the
development of new synthetic strategies which allow access to these heterocycles is of
interest to the pharmaceutical industry. The stereoselective synthesis of 3-substituted
1,2,3,4-tetrahydroisoquinolines (3, n = 1) and 2-substituted 2,3,4,5-tetrahydro-1Hbenzo[d]azepine (3, n = 2) was achieved starting from phthalan (1, n = 1) or isochroman
(1, n = 2) and chiral N-tert-butylsulfinyl aldimines, through a two-pot strategy: (1)
Reaction of the dianionic intermediate 4 resulting from the reductive opening lithiation of
phthalan2 or isochroman (1)3 with chiral aldimines in the presence of ZnMe2 to give
compounds 2 with high diastereoselectivity (dr 71:29-86:14) and (2) cyclization of the
aminoalcohol resulting from the removal of the tert-butylsulfinyl unit in enantiomerically
pure compounds 2.4 Regarding the stereochemistry of the major stereoisomer 2, it was
unambiguously determined by single X-ray analysis. Nucleophilic addition takes place to
the Re-face of the imine in the case of (Rs)-sulfinylimines. Hexahydropyrroloisoquinoline
6, hexahydropyridoisoquinoline 7 and octahydrobenzopyrroloazepine 8 were accessible
through this methodology starting from O-tetrahydropyranyl protected hydroxylimines 5,
taking place a final double cyclization.
( )n
O
1
OH O
( )n S
HN
1. Li, DTBB, 0 ºC
2. ZnMe2, 20 ºC
3. RCH=NS(O)t-Bu, -65 ºC
OLi
( )n
Li
4
N
THPO
(
O
S
1. HCl, MeOH, 20 ºC
2. Cl2SO, CHCl3, 50 ºC
3. NaOH/H2O, THF, 20 ºC
R
2
(53-90%)
N
N
( )n
NH
R
3
(51-80%)
N
)m
5
6 (60%)
7 (55%)
8 (51%)
m = 1, 2
n = 1, 2
R = Ph, i-Pr, CH3(CH2)7, Ph(CH2)2
1.
2.
3.
4.
Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
Almena, J.; Foubelo, F.; Yus, M., Tetrahedron 1995, 51, 3351-3364.
Almena, J.; Foubelo, F.; Yus, M., Tetrahedron 1995, 51, 3365-3374.
García, D.; Moreno, B.; Soler, T.; Foubelo, F.; Yus, M. Tetrahedron Lett. 2009, 50,
4710.