A COMPARISON OF DIELS-ALDER CATALYSTS GENERATED FROM LINEAR AND VAULTED BIARYLS AND BROMOBORANE-DIMETHYLSULFIDE COMPLEX

被引：29

作者：

BAO, JM ^{[1
]}

WULFF, WD ^{[1
]}

机构：

[1] UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 19期

关键词：

D O I：

10.1016/0040-4039(95)00534-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalysts prepared from the vaulted biaryls 2 and 3 and bromoborane dimethylsulfide were compared with that generated from the linear biaryl 1 for their ability to provide enantioselective induction in the Diels-Alder reaction of cyclopentadiene and methacrolein. The fact that the S-enantiomers of 2 and 3 give opposite induction than the S-enantiomer of 1 and the fact that effective catalysts can not be generated from 1 and phenylboron dichloride suggests that the catalysts from 2 and 3 do not have the same structure as the C-3-symmetrical catalyst 4 produced from 1.

引用

页码：3321 / 3324

页数：4

共 14 条

[1]

ALLINGER NL, 1992, J MOL STRUCT, V260, P161

[2]

BAO JD, UNPUB

[3] VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS [J].

BAO, JM ;

WULFF, WD ;

RHEINGOLD, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3814-3815

[4] THE LEWIS ACID COMPLEXES OF ALPHA,BETA-UNSATURATED CARBONYL AND NITRILE COMPOUNDS .1. A NUCLEAR MAGNETIC-RESONANCE STUDY [J].

CHILDS, RF ;

MULHOLLAND, DL ;

NIXON, A .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (06) :801-808

[5] 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

[6] CONFORMATIONAL STABILITY AND BARRIERS TO INTERNAL-ROTATION OF METHACROLEIN (CHO AND CDO) FROM FAR INFRARED SPECTRAL DATA, ABINITIO CALCULATIONS AND THE MICROWAVE-SPECTRUM OF METHACROLEIN D1 [J].

DURIG, JR ;

QIU, J ;

DEHOFF, B ;

LITTLE, TS .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1986, 42 (2-3) :89-103

[7] ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTION CATALYZED BY THE CHIRAL TITANIUM REAGENT [J].

IWASAWA, N ;

SUGIMORI, J ;

KAWASE, Y ;

NARASAKA, K .

CHEMISTRY LETTERS, 1989, (11) :1947-1950

[8] COMPARATIVE THEORETICAL-STUDY OF LEWIS ACID-BASE COMPLEXES OF BH3, BF3, BCL3, ALCL3, AND SO2 [J].

JONAS, V ;

FRENKING, G ;

REETZ, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8741-8753

[9] A BORATE PROPELLER COMPOUND AS CHIRAL CATALYST FOR AN ASYMMETRICALLY INDUCED DIELS-ALDER REACTION [J].

KAUFMANN, D ;

BOESE, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05) :545-546

[10] THEORETICAL-STUDIES OF CONFORMATIONS OF ACROLEIN, ACRYLIC-ACID, METHYL ACRYLATE, AND THEIR LEWIS ACID COMPLEXES [J].

LONCHARICH, RJ ;

SCHWARTZ, TR ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) :14-23

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