Atroposelectivity in the reactions of laterally lithiated tertiary amides

被引：39

作者：

Clayden, J

Pink, JH

机构：

[1] Department of Chemistry, University of Manchester, Manchester, M13 9PL, Oxford Road

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(97)00401-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lateral lithiation-electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation-alkylation reaction. (C) 1997 Elsevier Science Ltd.

引用

页码：2561 / 2564

页数：4

共 18 条

[1] [Anonymous], [No title captured]
[2] 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
[3] THE TERTIARY AMIDE AS AN EFFECTIVE DIRECTOR OF ORTHO LITHIATION
BEAK, P
BROWN, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) : 34 - 46
[4] BERG U, 1976, TETRAHEDRON LETT, P3197
[5] 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
[6] 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
[7] CLAYDEN J, IN PRESS ANGEW CHEM
[8] Ortho versus adjacent-benzylic directed lithiations of substituted N,N-diethylbenzamides
Court, JJ
Hlasta, DJ
[J]. TETRAHEDRON LETTERS, 1996, 37 (09) : 1335 - 1338
[9] 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
[10] LIQUID-CHROMATOGRAPHY ON TRIACETYLCELLULOSE .14. CHROMATOGRAPHIC-SEPARATION OF ENANTIOMERS AND BARRIERS TO ENANTIOMERIZATION OF AXIALLY CHIRAL AROMATIC CARBOXAMIDES
CUYEGKENG, MA
MANNSCHRECK, A
[J]. CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (05): : 803 - 809

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