Enantioselective addition of organozinc reagents to carbonyl compounds

被引：36

作者：

Yus, M

Ramón, DJ

机构：

[1] Univ Alicante, Fac Ciencias, Inst Sintesis Organ, E-03080 Alicante, Spain

[2] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

来源：

PURE AND APPLIED CHEMISTRY | 2005年 / 77卷 / 12期

关键词：

enantioselective; organozinc reagents; camphorsulfonamide; hydroxysulfon-amides; dialkylzinc; titanium tetraisopropoxide;

D O I：

10.1351/pac200577122111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Different chiral camphorsulfonamaide derivatives containing a hydroxy or a sulfonamido functionality, as well as chiral 1,2-hydroxysulfonamides, have been evaluated as chiral promoters in the classical enantioselective addition of dialkylzinc reagents to aldehydes in the presence of titanium tetraisopropoxide (ee up to 96 %). Surprisingly, ligands with a structure of isoborneol are able to promote the related unknown addition to ketones (ee > 99 %), the best ligand being the exo-diol derived from 1,2-trans-biscamphorsulfon-amidocyclohexane (HOCSAC).

引用

页码：2111 / 2119

页数：9

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