Abstract
Obtaining both enantiomers of a given compound in high enantiomeric
excess is an attractive and important challenge, because it is often
the case that each enantiomer exhibits different bioactivity. This
review summarizes some approaches to realize complete reversal of
enantioselectivity by changing various reaction conditions. Our
new approach to achieve reversal of enantioselection in the enantioselective
addition of diketene to aldehydes, affording optically active 5-hydroxy-3-keto
esters in high optical yield using Schiff bases that contain an
oxazoline moiety derived from l -serine,
is also described.
1 Introduction
2 Reversal Based on the Nature of the Substituent
2.1 Control with Catalyst Substituent
2.2 Control with Substrate Substituent
3 Control with Central Metal
4 Reversal of Enantioselectivity by Changing Reaction Conditions
4.1 Control with Solvent
4.2 Control with Temperature
4.3 Control with Additives
4.4 Control with Other Factors
5 Recent Concepts for Reversal of Enantioselectivity
5.1 Asymmetric Addition of Readily Available Nucleophiles with
Aldehydes
5.2 Enantioselectivity Reversal in Asymmetric Addition of Diketene
with Aldehydes
6 Conclusions and Outlook
Key words
enantioselective reaction - chiral ligand - Schiff
base - asymmetric C-C bond formation - oxazoline
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