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
收藏
页码：2111 / 2119
页数：9
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