Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis

RSC Advances Pub Date: 2016-03-07 DOI: 10.1039/C6RA00653A

Abstract

Various chiral oxazolidinones (Evans’ oxazolidinones) have been employed as effective chiral auxiliaries in the asymmetric alkylation of different enolates. This strategy has been found promising and successful when used as the key step (steps) in the total synthesis of several biologically active natural products. In this report, we try to underscore the applications of oxazolidinones as chiral auxiliaries in asymmetric alkylation, and particularly in the crucial chiral inducing steps in the total synthesis of natural products that show biological activities. Chiral auxiliaries are generally considered reliable compounds with well-known configurations, enabling and controlling the synthesis of a large number of enantiomerically pure compounds in a time-efficient manner. Consequently, the use of chiral auxiliaries are frequently considered a method of choice in the early phases of drug discovery.

Graphical abstract: Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis
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