The effect of the nitrogen substituent on enantioselectivity of the catalytic asymmetric reduction of meso-imides with chiral oxazaborolidine catalysts

ORGN 121

Simon Jones, simon.jones@sheffield.ac.uk and Barrie Marsh, chp04bjm@sheffield.ac.uk. Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, United Kingdom
Oxazaborolidine catalysts 1 have been used to assess the role of the nitrogen substituent on the enantioselective reduction of a range of meso-imides 2. After catalytic reduction of the meso-imides 2, intermediate hydroxy lactams were further reduced to their ã -lactams for ease of analysis.. Enantioselectivities depended greatly on nitrogen substituent (27-99%), however no variation in enantioselectivity is observed between oxazaborolidine catalysts 1. This methodology has been applied towards the synthesis of the Pharaohs ant pheromone, Monomorine III 3.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006