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
收藏
页码：559 / 562
页数：4
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