BORANES IN SYNTHESIS .2. ASYMMETRIC-SYNTHESIS OF BETA-AMINO ALCOHOLS - A FACILE CONVERSION OF ALPHA-AMINO ACETOPHENONES TO THE CORRESPONDING BETA-AMINO ALCOHOLS IN HIGH ENANTIOMERIC PURITY

被引：22

作者：

BEARDSLEY, DA

FISHER, GB

GORALSKI, CT

NICHOLSON, LW

SINGARAM, B

机构：

[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064

[2] DOW CHEM CO USA,MIDLAND,MI 48674

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(00)76745-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric reduction of 2-amino acetophenones with Ipc(2)BH or Ipc(2)BCl at -78 degrees C, yields the corresponding beta-amino alcohols in good to excellent yields. Although only modest (12-45% ee) enantiomeric excesses were obtained with Ipc(2)BH, 75-99% enantiomeric excesses were obtained when Ipc(2)BCl was used as the asymmetric reducing agent.

引用

页码：1511 / 1514

页数：4

共 25 条

[1] ASYMMETRIC REDUCTION OF ALPHA-KETO ESTERS WITH POTASSIUM 9-O-(1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSYL)-9-BORATABICYCLO[3.3.1]NONANE - CHIRAL SYNTHESIS OF ALPHA-HYDROXY ESTERS WITH OPTICAL PURITY APPROACHING 100-PERCENT EE [J].