Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to α,β-unsaturated aldehydes
Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to α,β-unsaturated aldehydes
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DOI：
10.1021/ja055291w
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发表时间：
2005-11-16
影响因子：
15
通讯作者：
Jorgensen, KA
中科院分区：
文献类型：
--
作者：
Marigo, M;Schulte, T;Jorgensen, KA
报道了有机催化的不对称多组分多米诺反应和α，β-不饱和醛的共轭加成反应.该开发首先基于有机催化的高度对映选择性亲核硫醇加成到亚胺鎓离子中间体中的β-碳原子上，然后将α-碳原子亲电胺化为烯胺中间体。多组分反应继续以中等至良好的产率得到对映体纯的氨基硫醇。此外，有机催化的硫醇加成到α，β-不饱和醛以良好的产率和优异的对映选择性进行。
An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to α,β-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the β-carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the α-carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino−thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to α,β-unsaturated aldehydes takes place in good yields and excellent enantioselectivities.