Stereoselective reactions .28. Effects of the alkyl group at the amide nitrogen of chiral bidentate lithium amides on enantioselective deprotonation reaction

被引：29

作者：

Aoki, K ^{[1
]}

Tomioka, K ^{[1
]}

Noguchi, H ^{[1
]}

Koga, K ^{[1
]}

机构：

[1] UNIV TOKYO, GRAD SCH PHARMACEUT SCI, BUNKYO KU, TOKYO 113, JAPAN

来源：

TETRAHEDRON | 1997年 / 53卷 / 40期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4020(97)00901-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective deprotonation of 4-substituted cyclohexanones (1a similar to d) by chiral bidentate lithium amides ((R)-2a similar to j) having an alkyl- or a fluoroalkyl substituent at the amide nitrogen was examined. (R)-2i having a 2,2,2-trifluoroethyl group at the amide nitrogen was found to be an excellent chiral base for the present deprotonation reaction. Structures of(R)-2i in solution and solid state are discussed. (C) 1997 Elsevier Science Ltd.

引用

页码：13641 / 13656

页数：16

共 90 条

[51] ENANTIOSELECTIVE FORMATION OF CIS-3,5-DIMETHYLCYCLOHEXANONE LITHIUM ENOLATE AND STEREOSELECTIVE ALDOL REACTION WITH BENZALDEHYDE
MAJEWSKI, M
GLEAVE, DM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3599 - 3605
[52] MAJEWSKI M, 1995, TETRAHEDRON LETT, V36, P5465
[53] SYNTHESIS OF TROPANE ALKALOIDS VIA ENANATIOSELECTIVE DEPROTONATION OF TROPINONE
MAJEWSKI, M
LAZNY, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) : 5825 - 5830
[54] SYNTHESIS OF BUTENOLIDES VIA ENANTIOSELECTIVE DEPROTONATION OF PROTECTED 4-HYDROXYCYCLOHEXANONE
MAJEWSKI, M
IRVINE, NM
MACKINNON, J
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (08) : 1837 - 1840
[55] MAJEWSKI M, 1991, SYNLETT, P173
[56] SYNTHESIS OF PYRANOTROPANES VIA ENANTIOSELECTIVE DEPROTONATION STRATEGY
MAJEWSKI, M
LAZNY, R
[J]. TETRAHEDRON LETTERS, 1994, 35 (22) : 3653 - 3656
[57] ENANTIOSELECTIVE DEPROTONATION OF PROTECTED 4-HYDROXYCYCLOHEXANONES
MAJEWSKI, M
MACKINNON, J
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (07): : 1699 - 1704
[58] ASYMMETRIC CLEAVAGE OF 9-AZABICYCLO[3.3.1]NONAN-3-ONE INTO CIS-2,6-DISUBSTITUTED PIPERIDINE - A FACILE APPROACH TO A CHIRAL BUILDING BLOCK FOR ALKALOID SYNTHESIS
MOMOSE, T
TOYOOKA, N
HIRAI, Y
[J]. CHEMISTRY LETTERS, 1990, (08) : 1319 - 1322
[59] MOMOSE T, 1990, CHEM PHARM BULL, V38, P2072
[60] TRIFLUOROMETHYL GROUP INDUCED HIGHLY STEREOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS
MORIZAWA, Y
YASUDA, A
UCHIDA, K
[J]. TETRAHEDRON LETTERS, 1986, 27 (16) : 1833 - 1836

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