Diastereoselective photocycloaddition of an axial chiral enamide

被引：57

作者：

Bach, T ^{[1
]}

Schröder, J ^{[1
]}

Harms, K ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 51期

关键词：

asymmetric induction; cycloadditions; photochemistry; atropisomerism;

D O I：

10.1016/S0040-4039(99)01933-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The axial chiral enamide 3 was prepared from 2-t-butylaniline in two steps (58% overall yield). Its photocycloaddition to benzaldehyde yielded the oxetane 4a as the major product (62% de), the structure of which was elucidated by single X-ray crystallography. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：9003 / 9004

页数：2

共 8 条

[1] Photocycloaddition of N-acyl enamines to aldehydes and its application to the synthesis of diastereomerically pure 1,2-amino alcohols
Bach, T
Schröder, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) : 1265 - 1273
[2] Clayden J, 1998, SYNLETT, P810
[3] Non-biaryl atropisomers: New classes of chiral reagents, auxiliaries, and ligands?
Clayden, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (09): : 949 - 951
[4] Rotational features of carbon-nitrogen bonds in axially chiral o-tert-butyl anilides and related molecules.: Potential substrates for the 'prochiral auxiliary' approach to asymmetric synthesis
Curran, DP
Hale, GR
Geib, SJ
Balog, A
Cass, QB
Degani, ALG
Hernandes, MZ
Freitas, LCG
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (23) : 3955 - 3975
[5] ATROPOSELECTIVE THERMAL-REACTIONS OF AXIALLY TWISTED AMIDES AND IMIDES
CURRAN, DP
QI, HY
GEIB, SJ
DEMELLO, NC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) : 3131 - 3132
[6] Eliel E.L., 1994, STEREOCHEMISTRY ORGA, P1119
[7] Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles
Fujita, M
Kitagawa, O
Izawa, H
Dobashi, A
Fukaya, H
Taguchi, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (10) : 1949 - 1952
[8] Atropisomeric amides:: stereoselective enolate chemistry and enantioselective synthesis via a new SmI2-mediated reduction
Hughes, AD
Price, DA
Simpkins, NS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10): : 1295 - 1304

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