# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004
L-proline catalyzed asymmetric transfer aldol reaction between
diacetone alcohol and aldehydes:
S. Chandrasekhar, * Ch. Narsihmulu, N. Ramakrishna Reddy and S. Shameem
Sultana.
Indian Institute of Chemical Technology, Hyderabad-500 007, India.
Fax: (+91)-40-27160512; E-mail: srivaric@iict.res.in
General:
The following chemicals were purchased from Aldrich and used as supplied: Lproline,
4-nitrobenzaldehyde,
2-chloro-5-nitrobenzaldehyde,
isobutyraldehyde,
cyclohexyl carboxaldehyde and freshly distilled diacetone alcohol.
1
H NMR spectra were recorded as solutions in CDCl3 at room temperature on a
Varian Gemini spectrometer at 200 MHz, Brucker 300 MHz, and mass spectra were
recorded on Finnigan MAT 1020B or micro mass VG 70-70H spectrometer operating at
70eV using direct inlet system.
ee of the products determined by chiral HPLC analysis using chiralcel OB-H column.
Physical data of the products are as follows:
4-Hydroxy-4- (4’-nitrophenyl)-butan-2-one: Spectral data are identical to authentic
sample and to those previously reported.1
4-Hydroxy-4- (4’-bromophenyl)-butan-2-one: Spectral data are identical to authentic
sample and to those previously reported. 1
4-Hydroxy-4- (2’-chlorophenyl)-butan-2-one: Spectral data are identical to authentic
sample and to those previously reported. 1
4-Hydroxy-4-(3’-nitro-phenyl)-butan-2-one: Spectral data are identical to authentic
sample and to those previously reported. 1
(4R)-4-(Cyclohexyl)-4-hydroxy-2-butanone: Spectral data are identical to authentic
sample and to those previously reported. 1
# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004
4-Hydroxy-5-methyl-hexan-2-one: Spectral data are identical to authentic sample and to
those previously reported. 1
4-Hydroxy-4-(2’-nitro-phenyl)-butan-2-one: Spectral data are identical to authentic
sample and to those previously reported.2
4-Hydroxy-4-(4’- methoxy-phenyl)-butan-2-one: Spectral data are identical to
authentic sample and to those previously reported.2
4-Hydroxy-4-(2’- chloro- 5’-nitro-phenyl)-butan-2-one:
1
H NMR (CDCl3, 200 MHz): δ 8.58-8.52 (m, 1H), 8.16-8.04 (m, 1H), 7.44 (d, J= 9.6 Hz,
1H),
5.43 (d, J= 12.0 Hz, 1H), 3.65 (bs, 1H), 3.08-2.52 (m, 2H),
2.24 (s,3H).
EI MS :
m/z 243 (M+),183, 43.
Enantiomeric excess:
64 % determined by HPLC using chiralcel OB-H column
(Hexane: isopropanol / 80: 20), tR = 6.37 (major), tR = 7.01
(minor).
References:
1. Z. Tang, F. Jiang, L. Yu, X. Cui, L. Gong, A. Mi, Y. Jiang and Y. Wu, J. Am.
Chem. Soc., 2003, 125, 5262.
2. P. Kotrusz, I. Kmentova, B. Gotov, S. Toma and E. Solcaniova, Chem. Commun.,
2002, 2510.