Rh(II)-catalyzed intramolecular N-H insertion of D-glucose-derived δ-amino α-diazo β-ketoester:: Synthesis of pyrrolidine iminosugars

被引：18

作者：

Vyavahare, Vinod P.

Chattopadhyay, Subrata

Puranik, Vedavati G.

Dhavale, Dilip D. ^{[1
]}

机构：

[1] Univ Pune, Dept Chem, Garware Res Ctr, Pune 411007, Maharashtra, India

[2] Bhabha Atom Res Ctr, Bioorgan Div, Bombay 400085, Maharashtra, India

[3] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India

来源：

SYNLETT | 2007年 / 04期

关键词：

alkaloids; azasugars; carbohydrates; pyrrolidines; rhodium carbenoid; N-H insertion;

D O I：

10.1055/s-2007-970743

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rhodium acetate catalyzed reaction of D-glucose-derived delta-amino alpha-diazo beta-ketoester allows a stereoselective beta-facial intramolecular N-H insertion reaction that leads to formation of the bicyclic pyrrolidinone ring skeleton in high yield. The sugar-substituted pyrrolidinone thus obtained was elaborated to allow the synthesis of promising glycosidase inhibitors, namely, 2,5-dideoxy2,5-imino-L-glycero-alpha-D-galactoheptitol and 2,5-dideoxy-2,5-imino-D-galactitol.

引用

页码：559 / 562

页数：4