Quantum Mechanical Transition-State Analysis Reveals the Precise Origin of Stereoselectivity in Chiral Quaternary Cinchonidinium Phase-Transfer Catalyzed Enolate Allylation

被引：31

作者：

Cook, Thomas C. ^{[1
]}

Andrus, Merritt B. ^{[1
]}

Ess, Daniel H. ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 23期

关键词：

ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; DENSITY FUNCTIONALS; CINCHONA ALKALOIDS; ALKYLATION; AMMONIUM;

D O I：

10.1021/ol3026582

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Density functional theory was used to model glycinate enolate binding and enantiomeric allylation transition states mediated by the cinchonidinium phase-transfer catalyst 2. Transition states show oxy-anion-ammonium interactions in contrast to pi-face interactions in the ground states. The details of stereoselectivity are described within the quaternary ammonium-tetrahedron face model.

引用

页码：5836 / 5839

页数：4

共 2 条

[1] Pentanidium-Catalyzed Asymmetric Phase-Transfer Conjugate Addition: Prediction of Stereoselectivity via DFT Calculations and Docking Sampling of Transition States, and Origin of Stereoselectivity
Kee, Choon Wee
Wong, Ming Wah
AUSTRALIAN JOURNAL OF CHEMISTRY, 2016, 69 (09) : 983 - 990
[2] Highly selective preparation of a chiral quaternary allyl aryl piperidinedione by palladium-catalyzed asymmetric allylation under solid-liquid phase-transfer catalysis
Nowicki, Audrey
Keldenich, Jerome
Agbossou-Niedercorn, Francine
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) : 6124 - 6127

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