Remarkable optical induction in the reduction of. alpha.-oxo esters with B-(3-pinanyl)-9-borabicyclo [3.3. 1] nonane. Synthesis of. alpha.-hydroxy esters of 100% …
HC Brown, GG Pai, PK Jadhav
Index: Brown, Herbert C.; Pai, Ganesh G.; Jadhav, Prabhakar K. Journal of the American Chemical Society, 1984 , vol. 106, # 5 p. 1531 - 1533
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Citation Number: 56
Abstract
Based on [~ Y]~~ D-5. 0 5~(neat, I= l)," Based on [~~]~~~-7. 0 6" exploring the effect of various electron-withdrawing substituents, we discovered that the a-keto esters are reduced to the corresponding a-hydroxy esters rapidly by Alpine-Borane. 2a The first compound of this class we studied was ethyl pyruvate (2, R= C, H,; eq 1). The compound underwent a rapid reduction
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