Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence

被引：12

作者：

Asensio, G ^{[1
]}

Cuenca, A ^{[1
]}

Rodriguez, N ^{[1
]}

Medio-Simòn, M ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 24期

关键词：

ASYMMETRIC PROTONATION; ACID; RESOLUTION; ARYLATION; EPOXIDES; KETONES;

D O I：

10.1016/j.tetasy.2003.09.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective protonation with 2-sulfinyl alcohols of lithium enolates of 2-arylcyclohexanones with different substituents on the phenyl group takes place with excellent enantio selectivities (89-99%). Chiral 2-phenylcyclohexanone and 2-arylcyclohexanones carrying electron donor substituents on the aromatic ring are converted into the corresponding trans-2-arylcyclohexanols by diastereoselective reduction with sodium naphthalenide in the presence of acetamide. The stereochemical integrity of the tertiary stereocenter is fully preserved using this reduction procedure. Interestingly, the chiral proton source is not consumed in the synthesis. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：3851 / 3855

页数：5

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