Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes
Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes
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DOI：
10.1021/ol050203y
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发表时间：
2005-03-31
期刊：
影响因子：
5.2
通讯作者：
Kwon, O
中科院分区：
文献类型：
--
作者：
Zhu, XF;Henry, CE;Kwon, O
膦催化的丙二烯酸酯与醛的反应以优异至中等的产率提供（2，6-二芳基-[1，3]二氧杂环己烷-4-亚基）-乙酸酯4，具有完全的非对映选择性和高E/Z-选择性。在除去该多米诺反应产物4中的缩醛官能团后，得到δ-羟基-β-酮酯11。报道的基于乙烯基膦的方法提供了一种新的方法来实现6-羟基-β-酮酯的合成，不同于经典的基于二阴离子的方法。
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, delta-hydroxy-beta-ketoester 11 was obtained. The reported vinylphosphonium-based approach provides a new way to achieve a synthesis of 6-hydroxy-beta-ketoesters that differs from the classical dianion-based approach.