Double Hetero-Michael Addition of N-Substituted Hydroxylamines to Quinone Monoketals: Synthesis of Bridged Isoxazolidines

被引：38

作者：

Yin, Zhiwei ^{[1
,2
]}

Zhang, Jinzhu ^{[1
,2
]}

Wu, Jing ^{[1
,2
]}

Liu, Che ^{[1
,2
]}

Sioson, Kate ^{[1
,2
]}

Devany, Matthew ^{[1
,2
]}

Hu, Chunhua ^{[3
]}

Zheng, Shengping ^{[1
,2
]}

机构：

[1] CUNY Hunter Coll, Dept Chem, New York, NY 10065 USA

[2] CUNY, Grad Ctr, New York, NY 10016 USA

[3] NYU, Dept Chem, New York, NY 10003 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 14期

关键词：

CONJUGATE ADDITION; NAPHTHOQUINONE ANTIBIOTICS; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITION REACTIONS; GRIGNARD-REAGENTS; DERIVATIVES; OXIDATION; MONOACETALS; ALKALOIDS; CHEMISTRY;

D O I：

10.1021/ol401235z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general synthesis of bridged isoxazolidines from a double hetero-Michael addition of N-substituted hydroxylamines to quinone monoketals has been developed. The different addition order of N-benzylhydroxylamine and N-Boc hydroxylamine is also discussed. Moreover, the various functionalities in the isoxazolidine products allow facile derivatization.

引用

页码：3534 / 3537

页数：4