Palladium(II)-catalyzed highly regio- and diastereoselective Cyclization of difunctional allylic N-tosylcarbamates.: A convenient synthesis of optically active 4-vinyl-2-oxazolidinones and total synthesis of 1,4-dideoxy-1,4-imino-L-xylitol

被引：51

作者：

Lei, AW ^{[1
]}

Liu, GS ^{[1
]}

Lu, XY ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 03期

关键词：

D O I：

10.1021/jo0161429

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd(II)-catalyzed cyclization of difunctional allylic N-tosyl carbamates in the presence of halide ions was developed with high regio- and diastereoselectivity. The reaction involves aminopalladation of alkene and beta-heteroatom elimination to regenerate Pd(II) species. When the readily available homochiral alcohols were used as substrates, highly optically active 4-vinyl-2-oxazolidinones were easily obtained. The utility of this method was exemplified by the convenient synthesis of 1,4-dideoxy-1,4-imino-L-xylitol.

引用

页码：974 / 980

页数：7

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