AN ASYMMETRIC-SYNTHESIS OF MK-0417 - OBSERVATIONS ON OXAZABOROLIDINE-CATALYZED REDUCTIONS

被引：155

作者：

JONES, TK

MOHAN, JJ

XAVIER, LC

BLACKLOCK, TJ

MATHRE, DJ

SOHAR, P

JONES, ETT

REAMER, RA

ROBERTS, FE

GRABOWSKI, EJJ

机构：

[1] Merck Sharp & Dohme Research Laboratories, Rahway

[2] Glaxo, Inc., Research Triangle Park, NC 27709

来源：

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

关键词：

D O I：

10.1021/jo00002a050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure MK-0417 has been prepared in nine steps from thiophene. The key reactions in the sequence were an oxazaborolidine-catalyzed borane reduction followed by a tosylation/amine displacement. The borane reduction was studied in detail, and observations regarding substituents on the oxazaborolidine catalyst and the intricacies of the reaction are reported, as well as a mild method for recovering the enantiomerically pure amino alcohol derived from the catalyst.

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页码：763 / 769

页数：7

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