Organic letters

Phosphine-catalyzed synthesis of 1, 3-dioxan-4-ylidenes

XF Zhu, CE Henry, J Wang, T Dudding, O Kwon

Index: Zhu, Xue-Feng; Henry, Christopher E.; Wang, Jay; Dudding, Travis; Kwon, Ohyun Organic Letters, 2005 , vol. 7, # 7 p. 1387 - 1390

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Citation Number: 131

Abstract

A phosphine-catalyzed reaction of an allenoate with aldehydes furnished (2, 6-diaryl-[1, 3] dioxan-4-ylidene)-acetates 4 in excellent to moderate yields with complete diastereoselectivity and high E/Z-selectivities. Upon removal of the acetal functionality in this domino reaction product 4, δ-hydroxy-β-ketoester 11 was obtained. The reported vinylphosphonium-based approach provides a new way to achieve a synthesis of δ- ...