CHIRAL LEWIS-ACIDS DERIVED FROM 1,8-NAPHTHALENEDIYLBIS(DICHLOROBORANE) - MECHANISTIC ASPECTS

被引：46

作者：

REILLY, M ^{[1
]}

OH, T ^{[1
]}

机构：

[1] SUNY BINGHAMTON,DEPT CHEM,BINGHAMTON,NY 13902

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 02期

关键词：

D O I：

10.1016/0040-4039(94)02227-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral Lewis acids derived from 1,8-Naphthalenediylbis(dichloroborane), a novel bidentate Lewis acid, have been found to be active catalysts for the asymmetric Diels-Alder reaction. Utilizing chiral ligands derived from amino acids, a range of enantioselectivities have been achieved with cyclopentadiene and various alpha,beta-unsaturated aldehydes. Some mechanistic aspects of this novel asymmetric bidentate catalyst have been addressed.

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页码：221 / 224

页数：4

相关论文

共 33 条

[1] AN EXAMPLE OF ACETALDEHYDE BRIDGING 2 METAL ATOMS - SYNTHESES AND THE X-RAY CRYSTAL-STRUCTURE OF "MO2(CO)4(MU,ETA-2-MECHO)(ETA-C5H5)2 [J].

ADAMS, H ;

BAILEY, NA ;

GAUNTLETT, JT ;

WINTER, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (20) :1360-1361

[2] COORDINATION AND INTERCONVERSION OF A KETONIC GROUPING BETWEEN ONE AND 2 TRANSITION-METAL ATOMS [J].

ADAMS, RD ;

CHEN, G ;

CHEN, LF ;

WU, WG ;

YIN, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9406-9408

[3]

BALASUBRAMANIYA.V, 1966, CHEM REV, V66, P567

[4] MULTIDENTATE LEWIS-ACIDS - CRYSTAL-STRUCTURE OF THE 2-1 ADDUCT OF 1,2-PHENYLENEDIMERCURY DICHLORIDE WITH TETRAPHENYLPHOSPHONIUM CHLORIDE [J].

BEAUCHAMP, AL ;

OLIVIER, MJ ;

WUEST, JD ;

ZACHARIE, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (01) :73-77

[5] TRANSITION STRUCTURES OF THE LEWIS ACID-CATALYZED DIELS-ALDER REACTION OF BUTADIENE WITH ACROLEIN - THE ORIGINS OF SELECTIVITY [J].

BIRNEY, DM ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4127-4133

[6] 1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].

COREY, EJ ;

LOH, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967

[7] THE ORIGIN OF GREATER THAN 200/1 ENANTIOSELECTIVITY IN A CATALYTIC DIELS-ALDER REACTION AS REVEALED BY PHYSICAL AND CHEMICAL STUDIES [J].

COREY, EJ ;

LOH, TP ;

ROPER, TD ;

AZIMIOARA, MD ;

NOE, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8290-8292

[8] THE STRUCTURE OF THE 2-METHYLACROLEIN BORON-TRIFLUORIDE COMPLEX IN THE CRYSTALLINE PHASE AND IN SOLUTION [J].

COREY, EJ ;

LOH, TP ;

SARSHAR, S ;

AZIMIOARA, M .

TETRAHEDRON LETTERS, 1992, 33 (46) :6945-6948

[9] DIMERIC (ETA-2-BENZOPHENONE)ZIRCONOCENE - ITS REMARKABLE STRUCTURE AND CHEMISTRY [J].

ERKER, G ;

DORF, U ;

CZISCH, P ;

PETERSEN, JL .

ORGANOMETALLICS, 1986, 5 (04) :668-676

[10] TRANSITION-STATE PI-SOLVATION BY AROMATIC RINGS - AN ELECTRONIC CONTRIBUTION TO DIELS-ALDER REACTION DIASTEREOSELECTIVITY [J].

EVANS, DA ;

CHAPMAN, KT ;

HUNG, DT ;

KAWAGUCHI, AT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1184-1186

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