Direct Catalytic Asymmetric Intramolecular Conjugate Addition of Thioamide to α,ss-Unsaturated Ester
Direct Catalytic Asymmetric Intramolecular Conjugate Addition of Thioamide to α,ss-Unsaturated Ester
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硫代酰胺与 α,ss-不饱和酯的直接催化不对称分子内共轭加成
DOI：
10.1002/chem.201102332
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
M.
中科院分区：
文献类型：
--
作者：
Suzuki;Y.; Yazaki;R.; Kumagai;N.; Shibasaki;M.
质子转移允许有效地访问光学活性的五元和六元环系统轴承酯和硫代酰胺功能在反的方式，这些环系统是经得起差分官能团操作。报道了硫代酰胺与α，β-不饱和酯的直接催化不对称分子内共轭加成反应。通过催化去质子化原位生成的Cu硫代酰胺烯醇化物经历共辄加成/质子化，以实现完全转化（参见方案）。
Proton transfer allows efficient access to optically active five-and six-membered ring systems bearing ester and thioamide functionalities in an anti fashion; these ring systems are amenable to differential functional group manipulation. Direct catalytic, asymmetric, intramolecular conjugate addition of thioamide to α, β-unsaturated esters is described. In situ generated Cu thioamide enolate, by catalytic deprotonation, underwent the conjugate addition/protonation, to achieve the complete transformation (see scheme).