Organic letters

Distinct Chemoselectivities in the Platinum-Catalyzed 1, 2-Carboalkoxylations of 5-Alkoxypent-1-yn-3-ol Derivatives

CM Ting, CD Wang, R Chaudhuri, RS Liu

文献索引：Ting, Chun-Ming; Wang, Chiou-Dong; Chaudhuri, Rupsha; Liu, Rai-Shung Organic Letters, 2011 , vol. 13, # 7 p. 1702 - 1705

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被引用次数: 22

摘要

Two distinct Pt-catalyzed carboalkoxylations of alkynes are reported. The cycloisomerization of 5-alkoxypent-1-yn-3-ol derivatives 5 produces 2, 6-dioxabicyclo [3.1. 0] hexanes 6; the mechanism is postulated to involve a hydroxyl-triggered [3.3]-sigmatropic allyl rearrangement. As the same catalysis is extensible to their tertiary alcohol analogues 7, distinct dihydrofuranyl alcohols 8 were obtained through a [3.3]-allyl rearrangement that is ...