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咪唑烷酮催化环状α,β-不饱和酮还原反应中立体选择性的起源

Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones.

作者信息

Gutierrez Osvaldo, Iafe Robert G, Houk K N

机构信息

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

出版信息

Org Lett. 2009 Oct 1;11(19):4298-301. doi: 10.1021/ol901586t.

Abstract

The organocatalytic transfer hydrogenation reactions of 3-phenyl-2-cyclopentenone with imidazolidinone catalysts are evaluated using the hybrid density functional (B3LYP/6-31G(d)) theory. The origin of the preference for the (E) iminium transition state is determined, and the stereoselectivity of hydride transfer is investigated.

摘要

使用杂化密度泛函(B3LYP/6-31G(d))理论评估了3-苯基-2-环戊烯酮与咪唑烷酮催化剂的有机催化转移氢化反应。确定了(E)亚胺鎓过渡态偏好的起源,并研究了氢化物转移的立体选择性。

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本文引用的文献

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Highly enantioselective transfer hydrogenation of alpha,beta-unsaturated ketones.
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Metal-free, organocatalytic asymmetric transfer hydrogenation of alpha,beta-unsaturated aldehydes.
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