Annulations of Enantioenriched Allenylsilanes with in Situ Generated Iminium Ions: Stereoselective Synthesis of Diverse Heterocycles

被引：30

作者：

Brawn, Ryan A.

Panek, James S. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

ASYMMETRIC-SYNTHESIS; FUNCTIONALIZED PYRROLIDINES; ALLENES; CYCLIZATION; 3-COMPONENT; DERIVATIVES; ALDEHYDES; ESTER;

D O I：

10.1021/ol802618p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioenriched allenylsilanes; participate in Lewis acid mediated annulations with in situ generated iminium ions derived from tertbutyl carbamate and methyl carbamate to selectively form functionalized 4,5-dihydropyrroles and 4,5-dihyrooxazines, respectively. The dihydropyrrole products were further elaborated in a stereocontrolled vinylsilane terminated cyclization with in situ generated oxonium ions, resulting in pyranopyrroles.

引用

页码：473 / 476

页数：4

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