Page 150 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant
P. 150
Catalysts for Fine Chemical Synthesis: Hydrolysis, Oxidation and Reduction. Volume 1
Edited by Stan M Roberts and Geraldine Poignant
Copyright 2002 John Wiley & Sons, Ltd.
ISBN: 0-471-98123-0
10 Asymmetric Reduction of Ketones
Using Bakers' Yeast
CONTENTS
10.1 Bakers' Yeast Reduction of Ethyl Acetoacetate . . . . . . . . . 137
10.2 Enantioselective synthesis of (Z)-N-carbobenzyloxy-3-hydroxyproline
ethyl ester
Mukund P. Sibi and James W. Christensen . . . . . . . . . . . 140
10.2.1 Immobilization of bakers' yeast . . . . . . . . . . . . . . 140
10.2.2 Bakers' yeast reduction of (Z)-N-carbobenzyloxy-3-ketoproline
ethyl ester . . . . . . . . . . . . . . . . . . . . 140
References . . . . . . . . . . . . . . . . . . . . . . . 142
10.1 BAKERS' YEAST REDUCTION OF ETHYL
ACETOACETATE
Among the strategies developed for the preparation of optically active ester
derivatives, the bakers' yeast reduction of the corresponding b-ketoesters is one
of the most useful methods. Because of its low cost, ready availability and its
utility, bakers' yeast can be considered as a relatively simple reagent which is
very easy to handle [1±3] .
O O , H OH O
Bakers Yeast
H 2 O, Sucrose
OEt OEt
Materials and equipment
. Ethyl acetoacetate, 9.8 mL, 10.0 g, 77 mmol
. Bakers' yeast (Saccharomyces cerevisiae), Sigma Type II, 20 g
. Sucrose, commercially available table sugar, 150 g
. Celite 1 or hyflo super cell, 20 g
. Tap water, 650 mL
. Sodium chloride
. Ethyl acetate, dichloromethane
. p-Anisaldehyde
