Conformationally interlocked amides: Remote asymmetric induction by mechanical transfer of stereochemical information

被引：64

作者：

Clayden, J ^{[1
]}

Pink, JH ^{[1
]}

Yasin, SA ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 1-2期

关键词：

D O I：

10.1016/S0040-4039(97)10443-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The axial conformation of an aromatic tertiary amide group may be powerfully influenced by an adjacent stereogenic centre. Because the amide axis can also control the formation of new chiral centres, the amide can act as a "relay centre" for the transmission of stereochemical information. Conformational interlocking of adjacent amide groups on an aromatic ring means that a pair of amide groups can be used in series to mediate asymmetric induction between remote stereogenic centres, for example those lying para across an aromatic ring. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：105 / 108

页数：4

共 30 条

[1] ACKERMAN JH, 1969, TETRAHEDRON LETT, P4487
[2] ACKERMAN JH, 1969, TETRAHEDRON LETT, P3879
[3] [Anonymous], [No title captured]
[4] HIDDEN AXIAL CHIRALITY AS A STEREODIRECTING ELEMENT IN REACTIONS INVOLVING ENOL(ATE) INTERMEDIATES .1. CYCLIZATION REACTIONS OF METHYL (4R)-3-(2-DIAZO-3-OXOBUTANOYL)THIAZOLIDINE-4-CARBOXYLATE AND RELATED-COMPOUNDS
BEAGLEY, B
BETTS, MJ
PRITCHARD, RG
SCHOFIELD, A
STOODLEY, RJ
VOHRA, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (15): : 1761 - 1770
[5] A COMPARISON OF SECONDARY AND TERTIARY AMIDES AS DIRECTORS OF ORTHO AND ADJACENT BENZYLIC LITHIATION AND OF ASYMMETRIC INDUCTION IN ORTHO LITHIATED BENZAMIDES
BEAK, P
TSE, A
HAWKINS, J
CHEN, CW
MILLS, S
[J]. TETRAHEDRON, 1983, 39 (12) : 1983 - 1989
[6] DIASTEREOISOMERIC ATROPISOMERS FROM THE ADDITION OF LITHIATED N,N-DIALKYL-1-NAPHTHAMIDES TO ALDEHYDES
BOWLES, P
CLAYDEN, J
TOMKINSON, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (50) : 9219 - 9222
[7] Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes
Bowles, P
Clayden, J
Helliwell, M
McCarthy, C
Tomkinson, M
Westlund, N
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (17): : 2607 - 2616
[8] Asymmetric induction using atropisomers: Diastereoselective additions to 2-acyl-1-naphthamides
Clayden, J
Westlund, N
Wilson, FX
[J]. TETRAHEDRON LETTERS, 1996, 37 (31) : 5577 - 5580
[9] Atroposelectivity in the reactions of laterally lithiated tertiary amides
Clayden, J
Pink, JH
[J]. TETRAHEDRON LETTERS, 1997, 38 (14) : 2561 - 2564
[10] 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

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