Reaction of acylsilanes with α-sulfinyl carbanions: regioselective synthesis of silyl enol ethers
作者:Mitsunori Honda、Tadashi Nakajima、Maiko Okada、Keita Yamaguchi、Mitsuhiro Suda、Ko-Ki Kunimoto、Masahito Segi
DOI:10.1016/j.tetlet.2011.05.041
日期:2011.7
The reaction of acylsilanes with α-sulfinyl carbanions such as α-lithioalkyl sulfoxide is described. The reaction proceeds to give silyl enol ethers preferentially through the initial formation of the α-silyl alkoxide intermediates. In particular, the products derived from enolizable acylsilanes were the regio-defined silyl enol ethers that cannot be obtained by usual enolization of the corresponding
描述了酰基硅烷与α-亚磺酰基碳负离子如α-硫代烷基亚砜的反应。反应通过首先形成α-甲硅烷基醇盐中间体而优先得到甲硅烷基烯醇醚。特别地,衍生自可烯丙基化的酰基硅烷的产物是区域限定的甲硅烷基烯醇醚,其不能通过将相应的不对称酮与碱进行常规烯醇化而获得。