Chiral enamide. Part 1: Epoxidations of chiral enamides. A viable approach to chiral nitrogen stabilized oxyallyl cations in [4+3] cycloadditions

被引：54

作者：

Xiong, H ^{[1
]}

Hsung, RP ^{[1
]}

Shen, LC ^{[1
]}

Hahn, JM ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 25期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(02)00849-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first study of stereoselective epoxidations of chiral enamides is described here. Its potential in the synthesis of chiral alpha-keto aminals as a viable approach to nitrogen stabilized oxyallyl cations in stereoselective [4+3] cycloadditions is also illustrated. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4449 / 4453

页数：5

共 68 条

[41]

RAINIER JD, 1999, ORG LETT, P1793

[42] NMR studies on epoxidations of allenamides. Evidence for formation of nitrogen-substituted allene oxide and spiro-epoxide via trapping experiments [J].

Rameshkumar, C ;

Xiong, H ;

Tracey, MR ;

Berry, CR ;

Yao, LJ ;

Hsung, RP .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1339-1345

[43]

Rappoport Z., 1994, CHEM ENAMINES CHEM F

[44]

Saalfrank R. W., 1993, METHODEN ORGANISCHEN, P3093

[45]

Schottelius MJ, 1998, HELV CHIM ACTA, V81, P2341, DOI 10.1002/(SICI)1522-2675(19981216)81:12<2341::AID-HLCA2341>3.0.CO

[46]

2-U

[47]

SEEBACH D, 2002, IN PRESS HELV CHIM A, V82

[48]

Stark CBW, 1998, ANGEW CHEM INT EDIT, V37, P1266, DOI 10.1002/(SICI)1521-3773(19980518)37:9<1266::AID-ANIE1266>3.0.CO

[49]

2-9

[50] Lewis acid-catalyzed ring-opening reactions of semicyclic N,O-acetals [J].

Sugiura, M ;

Kobayashi, S .

ORGANIC LETTERS, 2001, 3 (03) :477-480

← 1 2 3 4 5 6 7 →