An iterative catalytic route to enantiopure deoxypropionate subunits:: Asymmetric conjugate addition of Grignard reagents to α,β-unsaturated thioesters
An iterative catalytic route to enantiopure deoxypropionate subunits:: Asymmetric conjugate addition of Grignard reagents to α,β-unsaturated thioesters
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DOI：
10.1021/ja053020f
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发表时间：
2005-07-20
影响因子：
15
通讯作者：
Feringa, BL
中科院分区：
文献类型：
--
作者：
Mazery, RD;Pullez, M;Feringa, BL
本发明提供了格氏试剂（特别是MeMgBr）与α，β-不饱和硫酯的高对映选择性（高达96%ee）共轭加成，以及其在顺式和反式-1，3-二甲基阵列和脱氧丙酸酯亚基的非对映和对映选择性迭代路线中的应用。该方法的多功能性在（−）-lardolure（一种多甲基分支的昆虫天然信息素）的合成中得到了说明。
A highly enantioselective (up to 96% ee) conjugate addition of Grignard reagents, in particular, MeMgBr, to α,β-unsaturated thioesters is provided as well as its application to a diastereo- and enantioselective iterative route tosyn- andanti-1,3-dimethyl arrays and deoxypropionate subunits. The versatility of the method is illustrated in the synthesis of (−)-lardolure, a multimethyl-branched insect natural pheromone.