An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: Serendipity rules

被引：72

作者：

Nugent, WA ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Proc Res & Dev Dept, Chambers Works, Deepwater, NJ 08023 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 13期

关键词：

D O I：

10.1021/ol0259488

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.

引用

页码：2133 / 2136

页数：4

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