Organocatalytic asymmetric fulvene formation

被引：3

作者：

Sieverding, Paul ^{[1
]}

Osterbrink, Johanna ^{[1
]}

Koegerler, Paul ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Inorgan Chem, D-52074 Aachen, Germany

来源：

TETRAHEDRON | 2018年 / 74卷 / 43期

基金：

欧洲研究理事会;

关键词：

Fulvenes; Proline; Tertiary amines; Hydrogen bonding additives; Iminium catalysis; Reversal of enantioselectivity; ALDOL REACTIONS; PROPENE POLYMERIZATION; ENAMINE CARBOXYLATES; CATALYSIS; COMPLEXES; WATER; PENTAFULVENE; DERIVATIVES; SOLVENTS; VIEW;

D O I：

10.1016/j.tet.2018.09.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric formation of a fulvene from a racemic alpha,alpha-disubstituted aldehyde has been developed. Dynamic kinetic resolution of rac-2-phenylpropanal by a simple, modularly designed supramolecular organocatalyst consisting of inexpensive components has been established, producing the desired fulvene in good yields and moderate enantioselectivities. Herein we propose a mechanistic interpretation of the observed solvent- and additive-induced stereoselectivity reversal. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：6278 / 6287

页数：10

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