Acyclic stereoselection. 44. Diastereoselectivity in the ortho ester Claisen rearrangement of chiral propargylic alcohols. Use of. beta.-allenic esters as chiral …

MA Henderson, CH Heathcock

Index: Henderson, Mark, A.; Heathcock, Clayton, H. Journal of Organic Chemistry, 1988 , vol. 53, # 20 p. 4736 - 4745

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Citation Number: 45

Abstract

The diastereoselectivity of the ortho ester Claisen rearrangement of chiral propargylic alcohols has been investigated for alcohols 6-12 (eq 3). The results of this study, summarized in Table 11, show that aryl-substituted propargyl alcohols 11 and 12 react stereorandomly. However, alkyl-substituted propargyl alcohols 6-10 show a preference for formation of the 2S*, 4S* diastereomer, with stereoselectivity increasing with increasing ...

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