A PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF ALPHA,ALPHA-DIARYL-2-PYRROLIDINEMETHANOL - PREPARATION AND CHEMISTRY OF THE CORRESPONDING OXAZABOROLIDINES

被引：238

作者：

MATHRE, DJ

JONES, TK

XAVIER, LC

BLACKLOCK, TJ

REAMER, RA

MOHAN, JJ

JONES, ETT

HOOGSTEEN, K

BAUM, MW

GRABOWSKI, EJJ

机构：

[1] Merck Sharp & Dohme Research Laboratories, Department of Process Research and Development, Rahway

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 02期

关键词：

D O I：

10.1021/jo00002a049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical two-step enantioselective synthesis of alpha,alpha-diaryl-2-pyrrolidinemethanols (1) from proline, based on the addition of aryl Grignard reagents to proline-N-carboxanhydride (3), is reported. An investigation into the chemistry of the corresponding B-alkyl- and B-aryloxazaborolidines (2) led to the development of a reliable procedure for their preparation.

引用

页码：751 / 762

页数：12

共 34 条

[11]

COREY EJ, 1989, TETRAHEDRON LETT, V30, P6278

[12]

COREY EJ, 1987, J AM CHEM SOC, V109, P551

[13] AMINO-ALCOHOL ESTERS OF HYDROXYBORANES .9. SALICYLAMIDE-BORON-MANNICH-BASES AS POTENTIAL ANTI-TUMOR AGENTS [J].