Catalyst control in a chiral borane-mediated aldol reaction. Both syn- and anti-aldols in almost optically pure state obtained from one racemic aldehyde

被引：39

作者：

Kiyooka, S

Kira, H

Hena, MA

机构：

[1] Department of Chemistry, Faculty of Science, Kochi University, Kochi 780, Akebono-cho

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 15期

关键词：

D O I：

10.1016/0040-4039(96)00379-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral borane (L-2 and D-2)-mediated aldol reaction proceeded with chiral aldehydes (1, 5, and 9) in a manner of ''catalyst control''. Both enantiomers were obtained from one racemic aldehyde in almost optically pure state. Copyright (C) 1996 Elsevier Science Ltd

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页码：2597 / 2600

页数：4

相关论文

共 26 条

[1]

ANH NT, 1977, NOUV J CHIM, V1, P61

[2] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV) [J].

CARREIRA, EM ;

SINGER, RA ;

LEE, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8837-8838

[3]

Cherest M., 1968, TETRAHEDRON LETT, P2199

[4] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[5] STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS [J].

CRAM, DJ ;

ELHAFEZ, FAA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) :5828-5835

[6]

FURUTA K, 1991, SYNLETT, P439

[7] CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST [J].

FURUTA, K ;

MARUYAMA, T ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1041-1042

[8] REAGENT CONTROL IN THE ALDOL ADDITION-REACTION OF CHIRAL BORON ENOLATES WITH CHIRAL ALPHA-AMINO ALDEHYDES - TOTAL SYNTHESIS OF (3S,4S)-STATINE [J].

GENNARI, C ;

PAIN, G ;

MORESCA, D .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6248-6249

[9]

Heathcock C. H., 1984, ASYMMETRIC SYNTHESIS, V3, P111

[10] ACYCLIC STEREOSELECTION .16. HIGH DIASTEREOFACIAL SELECTIVITY IN LEWIS ACID MEDIATED ADDITIONS OF ENOLSILANES TO CHIRAL ALDEHYDES [J].

HEATHCOCK, CH ;

FLIPPIN, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) :1667-1668