Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes

被引：10

作者：

Kennington, Stuart C. D. ^{[1
]}

Teloxa, Saul F. ^{[1
]}

Mellado-Hidalgo, Miguel ^{[1
]}

Galeote, Oriol ^{[1
]}

Puddu, Sabrina ^{[1
]}

Bellido, Marina ^{[1
]}

Romea, Pedro ^{[1
]}

Urpi, Felix ^{[1
]}

Aullon, Gabriel ^{[2
]}

Font-Bardia, Merce ^{[3
]}

机构：

[1] Univ Barcelona, Dept Inorgan & Organ Chem, Sect Organ Chem, Carrer Marti i Franques 1-11, Barcelona 08028, Spain

[2] Univ Barcelona, Inorgan Chem Sect, Dept Inorgan & Organ Chem, Carrer Marti i Franques 1-11, Barcelona 08028, Spain

[3] Univ Barcelona, CCiTUB, Xray Diffract Unity, Carrer Sole & Sabaris 1-3, Barcelona 08028, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 28期

关键词：

aldol reaction; asymmetric catalysis; direct reaction; nickel; thiazinanethiones;

D O I：

10.1002/anie.202104352

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O-TIPS-protected anti-aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol.

引用

页码：15307 / 15312

页数：6

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