Chemistry Reference
In-Depth Information
8A
CATALYTIC ASYMMETRIC
CONJUGATE ADDITION
JIAN - XIN JI
Chendu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
ALBERT S. C. CHAN
Department of Applied Biology and Chemical Technology, The Hong Kong
Polytechnic University, Hong Kong
8A.1. INTRODUCTION
The catalytic asymmetric conjugate addition to
-unsaturated compounds is one of
the most powerful carbon - carbon and carbon - heteroatom bond - forming reactions in
organic synthesis. The reaction is enormously useful for the construction of enantioen-
riched, highly functionalized carbon skeletons for the total syntheses of numerous bio-
logically active compounds. The scope of the reaction is broad, owing to the availability
of a large variety of donor and acceptor compounds. The high potential of this synthetic
method is evident with the possibility of building
multiple
stereocenters in a single syn-
thetic operation, and many asymmetric catalytic systems can exhibit high reactivity and
stereoselectivity. In this chapter, recent advances in catalytic asymmetric conjugate
addition reactions are described according to four categories: (i) conjugate addition
of organometallics, (ii) conjugate addition of other carbon-centered nucleophiles, (iii)
tandem conjugate addition reactions, and (iv) conjugate addition of heteroatom
nucleophiles.
α
,
β
8A.2. CATALYTIC ASYMMETRIC CONJUGATE ADDITION
OF ORGANOMETALLICS
The catalytic asymmetric conjugate addition of organometallic reagents to electrophili-
cally activated olefi ns constitutes one of the most powerful methods for carbon-carbon
