Efficient asymmetric protonation of enolates with readily accessible chiral α-sulfinyl alcohols

被引：27

作者：

Asensio, G ^{[1
]}

Alemán, P ^{[1
]}

Cuenca, A ^{[1
]}

Gil, J ^{[1
]}

Medio-Simón, M ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(98)00426-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The efficient asymmetric protonation of lithium enolates of 2-alkylcycloalkanones (87-96% ee) with readily accessible chiral alpha-sulfinyl alcohols is described. Optimal stereoselection is achieved for each lithium enolate at a different reaction temperature in the range -40 to - 100 degrees C. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：4073 / 4078

页数：6

相关论文

共 17 条

[1] ASYMMETRIC INDUCTION IN THE REDUCTION OF BETA-OXOSULFOXIDES BY METAL-HYDRIDES [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (07) :1687-1690

[2]

[Anonymous], MODERN SYNTHETIC MET

[3] Remarkable effect of lithium bromide in the enantioselective protonation with α-sulfinyl alcohols [J].

Asensio, G ;

Aleman, PA ;

Domingo, LR ;

Medio-Simón, M .

TETRAHEDRON LETTERS, 1998, 39 (20) :3277-3280

[4]

ASENSIO G, IN PRESS J ORG CHEM

[5] ASYMMETRIC-SYNTHESIS OF OXYGEN-SUBSTITUTED AND NITROGEN-SUBSTITUTED DIFLUOROMETHYLENE PRODUCTS [J].

BRAVO, P ;

PREGNOLATO, M ;

RESNATI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2726-2731

[6]

Fehr C., 1996, Angew. Chem., V35, P2566

[7] STEREOSELECTIVE PROTONATION OF CARBANIONS .5. EFFECTS OF REACTION CONDITIONS ON THE ENANTIOSELECTIVE PROTONATION OF LACTONE ENOLATES [J].

GERLACH, U ;

HAUBENREICH, T ;

HUNIG, S .

CHEMISCHE BERICHTE, 1994, 127 (10) :1981-1988

[8] CHEMISTRY OF CARBANIONS .19. ALKYLATION OF ENOLATES FROM UNSYMMETRICAL KETONES [J].

HOUSE, HO ;

GALL, M ;

OLMSTEAD, HD .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (16) :2361-&

[9] Highly enantiofacial protonation of prochiral lithium enolates with chiral beta-hydroxy sulfoxides [J].

Kosugi, H ;

Hoshino, K ;

Uda, H .

TETRAHEDRON LETTERS, 1997, 38 (39) :6861-6864

[10] PREPARATION OF OPTICALLY-ACTIVE KETONES VIA ENANTIOFACE-DIFFERENTIATING PROTONATION OF PROCHIRAL ENOLATES [J].

MATSUMOTO, K ;

OHTA, H .

TETRAHEDRON LETTERS, 1991, 32 (36) :4729-4732