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三氟甲磺酸铋催化的2-(三甲基硅氧基)呋喃的非对映选择性Mukaiyama羟醛反应。

Diastereoselective Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan catalyzed by bismuth triflate.

作者信息

Ollevier Thierry, Bouchard Jean-Emmanuel, Desyroy Valerie

机构信息

Département de chimie, Université Laval, Québec, Canada G1K 7P4.

出版信息

J Org Chem. 2008 Jan 4;73(1):331-4. doi: 10.1021/jo702085p. Epub 2007 Dec 11.

Abstract

We have developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in low catalyst loading (1 mol %). The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl)furan-2(5H)-ones in high yields with good to very good diastereoselectivities (dr up to >98:2). Such selectivities, albeit previously reported with other Lewis acids, could this time be achieved with a much lower catalyst loading. 5-(Hydroxy(alkyl)methyl)furan-2(5H)-ones derived from ketones could also be obtained with good diastereoselectivities.

摘要

我们开发了一种高效的乙烯型Mukaiyama羟醛反应,该反应以三氟甲磺酸铋为催化剂,低催化剂负载量(1 mol%)介导2-(三甲基硅氧基)呋喃与各种芳香醛发生反应。反应进行迅速,能以高产率得到相应的5-(羟基(芳基)甲基)呋喃-2(5H)-酮,非对映选择性良好至非常好(非对映体比例高达>98:2)。尽管此前使用其他路易斯酸也有过此类选择性的报道,但此次在低得多的催化剂负载量下就实现了。由酮衍生得到的5-(羟基(烷基)甲基)呋喃-2(5H)-酮也能以良好的非对映选择性得到。

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