A Divergent Synthesis of Essentially Enantiopure syn-and anti-Propionate Aldol Adducts Based on the Chiral 1, 3, 2-Oxazaborolidin-5-one-Promoted Asymmetric …

S Kiyooka, KA Shahid

Index: Kiyooka; Shahid Bulletin of the Chemical Society of Japan, 2001 , vol. 74, # 8 p. 1485 - 1495

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Citation Number: 10

Abstract

Essentially, enantiopure syn-and anti-propionate aldol adducts were divergently synthesized using a novel strategy which utilizes both the highly enantioselective 1, 3, 2- oxazaborolidin-5-one-promoted aldol reaction with a ketene silyl acetal derived from ethyl 2- bromo propionate and a highly diastereoselective radical debromination reaction. These procedures provide yields that increase to a level available for practical synthesis.