Lithium N-trityl-N-(R)-1-phenethylamide, a readily available and useful base for the enantioselective formation of chiral enolates from achiral ketones

被引：30

作者：

Busch-Petersen, J ^{[1
]}

Corey, EJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 36期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)01185-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium N-trityl-N-(R)-1-phenylethylamide (6) is a readily available and useful reagent for the enantioselective (20:1) conversion of 4-t-butylcyclohexanone to the corresponding (S)-enolate. This reaction provides access to numerous useful chiral compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6941 / 6944

页数：4

共 16 条

[1] STEREOELECTRONIC INFLUENCE ON THE NABH4 REDUCTION STEREOSELECTIVITY OF ALICYCLIC BETA-KETOESTERS
BEESON, C
PHAM, N
DIX, TA
[J]. TETRAHEDRON LETTERS, 1992, 33 (21) : 2925 - 2928
[2] Brander M, 1918, RECL TRAV CH PAYS-BA, V37, P67
[3] Sterically shielded secondary N-tritylamines and N-tritylamide bases, readily available and useful synthetic reagents
Busch-Petersen, J
Corey, EJ
[J]. TETRAHEDRON LETTERS, 2000, 41 (15) : 2515 - 2518
[4] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES
CAIN, CM
COUSINS, RPC
COUMBARIDES, G
SIMPKINS, NS
[J]. TETRAHEDRON, 1990, 46 (02) : 523 - 544
[5] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE
COREY, EJ
GROSS, AW
[J]. TETRAHEDRON LETTERS, 1984, 25 (05) : 495 - 498
[6] Crabtree S.R, 1991, ORG SYNTH, V70, P256
[7] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[8] DALE JA, 1973, J AM CHEM SOC, V95, P112
[9] CHEMISTRY OF CARBANIONS .23. USE OF METAL-COMPLEXES TO CONTROL ALDOL CONDENSATION
HOUSE, HO
CRUMRINE, DS
TERANISH.AY
OLMSTEAD, HD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) : 3310 - 3324
[10] ELECTRON SPIN RESONANCE OF TRITYL ALKYL NITROXIDES . SPIN-LABELED AMINO ACIDS
MAENDER, OW
JANZEN, EG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) : 4072 - &

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