Chiral synthesis via organoboranes. 21. Allyl-and crotylboration of. alpha.-chiral aldehydes with diisopinocampheylboron as the chiral auxiliary

HC Brown, KS Bhat, RS Randad

Index: Brown, Herbert C.; Bhat, Krishna S.; Randad, Ramnarayan S. Journal of Organic Chemistry, 1989 , vol. 54, # 7 p. 1570 - 1576

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Citation Number: 238

Abstract

B-Allyldiisopinocampheylboranes [18, prepared from (+ Ia-pinene; 19, prepared from (-)-a- pinene] have been screened for diastereofacial selectivity in their reaction with a-substituted chiral aldehydes. Both syn and anti products have been obtained in very high diastereoselectivities. Further,(E)-crotyldiisopinocampheylboranes [20, prepared from (+)-a- pinene; 21, prepared from (-)+ pinene] and (2)-crotyldiisopinocampheylboranes[22, ...