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

[21] An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction
Kitagawa, O
Izawa, H
Taguchi, T
Shiro, M
[J]. TETRAHEDRON LETTERS, 1997, 38 (25) : 4447 - 4450
[22] DIRECTED ORTHO METALATION OF N,N-DIETHYLBENZAMIDES - SILICON PROTECTION OF ORTHO SITES AND THE ORTHO-METHYL GROUP
MILLS, RJ
TAYLOR, NJ
SNIECKUS, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) : 4372 - 4385
[23] DILITHIATED SYNTHONS OF TERTIARY BENZAMIDES, PHTHALAMIDES, AND O,O'-ARYL DICARBAMATES
MILLS, RJ
HORVATH, RF
SIBI, MP
SNIECKUS, V
[J]. TETRAHEDRON LETTERS, 1985, 26 (09) : 1145 - 1148
[24] NAD(P)+-NAD(P)H MODELS .57. STEREOCHEMISTRY IN (NET) HYDRIDE TRANSFER FROM AND TO NAD(P)+-NAD(P)H MODELS - CHIRALITY SINK
OHNO, A
KASHIWAGI, M
ISHIHARA, Y
USHIDA, S
OKA, S
[J]. TETRAHEDRON, 1986, 42 (04) : 961 - 973
[25] OKI M, 1983, TOP STEREOCHEM, V14, P1
[26] Pirkle William H., 1993, Journal of Chromatography, V648, P101, DOI 10.1016/0021-9673(93)83291-Y
[27] DIRECTED ORTHO METALATION - TERTIARY AMIDE AND O-CARBAMATE DIRECTORS IN SYNTHETIC STRATEGIES FOR POLYSUBSTITUTED AROMATICS
SNIECKUS, V
[J]. CHEMICAL REVIEWS, 1990, 90 (06) : 879 - 933
[28] NUCLEAR MAGNETIC RESONANCE STUDIES OF AMIDES
STEWART, WE
SIDDALL, TH
[J]. CHEMICAL REVIEWS, 1970, 70 (05) : 517 - &
[29] On ligand design for catalytic outer sphere reactions: A simple asymmetric synthesis of vinylglycinol
Trost, BM
Bunt, RC
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01): : 99 - 102
[30] VANLIER PM, 1983, RECL TRAV CHIM PAY B, V102, P337

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