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：

美国国家科学基金会; 美国国家卫生研究院;

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 [J].

BEESON, C ;

PHAM, N ;

DIX, TA .

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 [J].

Busch-Petersen, J ;

Corey, EJ .

TETRAHEDRON LETTERS, 2000, 41 (15) :2515-2518

[4] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES [J].

CAIN, CM ;

COUSINS, RPC ;

COUMBARIDES, G ;

SIMPKINS, NS .

TETRAHEDRON, 1990, 46 (02) :523-544

[5] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].

COREY, EJ ;

GROSS, AW .

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 [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

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 [J].

HOUSE, HO ;

CRUMRINE, DS ;

TERANISH.AY ;

OLMSTEAD, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) :3310-3324

[10] ELECTRON SPIN RESONANCE OF TRITYL ALKYL NITROXIDES . SPIN-LABELED AMINO ACIDS [J].

MAENDER, OW ;

JANZEN, EG .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) :4072-&

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