COMPLEXES CONTAINING A LEWIS-ACID AND BRONSTED ACID FOR THE CATALYTIC ASYMMETRIC DIELS-ALDER REACTION

被引：29

作者：

AGGARWAL, VK ^{[1
]}

ANDERSON, E ^{[1
]}

GILES, R ^{[1
]}

ZAPARUCHA, A ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM,TONBRIDGE TN11 9AN,KENT,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/0957-4166(95)00163-J

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Complexes containing a Lewis acid and a Bronsted acid have been prepared by the reaction of an amino alcohol and a trihaloborane. The structures of the complexes were determined by B-11, H-1, and C-13 analysis and shown to be the acyclic structures 5 rather than the possible cyclic structures 6 which only contain the single Lewis acid. A variety of amino alcohols were combined with BBr3 and BCl3 and tested in Diels Alder reactions between methacrolein and cyclopentadiene. Whilst very high exo selectivity was observed, enantioselectivity was variable depending on the amino alcohol used, Prolinol 4 gave the highest ee (97%) but quinidine gave the highest ee (64%) for a naturally occurring amino alcohol.

引用

收藏

页码：1301 / 1306

页数：6

相关论文

共 40 条

[1] CATIONIC MONONUCLEAR AND BINUCLEAR IRON COMPLEXES AS LEWIS ACID CATALYSTS IN MUKAIYAMA REACTIONS [J].

BACH, T ;

FOX, DNA ;

REETZ, MT .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) :1634-1636

[2] MULTIDENTATE LEWIS-ACIDS - ADDUCTS OF MONODENTATE AND BIDENTATE TITANIUM TRICHLOROALKOXIDES WITH KETONES [J].

BACHAND, B ;

WUEST, JD .

ORGANOMETALLICS, 1991, 10 (06) :2015-2025

[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] MULTIDENTATE LEWIS-ACIDS - SYNTHESIS AND STRUCTURE OF COMPLEX ALUMINUM-CHLORIDE ALKOXIDES [J].

BELANGERGARIEPY, F ;

HOOGSTEEN, K ;

SHARMA, V ;

WUEST, JD .

INORGANIC CHEMISTRY, 1991, 30 (22) :4140-4145

[5] SOLVENT EFFECTS ON A DIELS-ALDER REACTION FROM COMPUTER-SIMULATIONS [J].

BLAKE, JF ;

JORGENSEN, WL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7430-7432

[6] ENHANCED HYDROGEN-BONDING OF WATER TO DIELS-ALDER TRANSITION-STATES - AB-INITIO EVIDENCE [J].

BLAKE, JF ;

LIM, D ;

JORGENSEN, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :803-805

[7] EFFECT OF CHIRAL QUATERNARY AMMONIUM-SALTS ON (SALEN)MN-CATALYZED EPOXIDATION OF CIS-OLEFINS - A HIGHLY ENANTIOSELECTIVE, CATALYTIC ROUTE TO TRANS-EPOXIDES [J].

CHANG, SB ;

GALVIN, JM ;

JACOBSEN, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6937-6938

[8] ASYMMETRIC DIELS-ALDER REACTIONS OF CYCLOPENTADIENE WITH N-CROTONOYL AND N-ACRYLOYL-4,4-DIMETHYL-1,3-OXAZOLIDIN-2-ONE, MEDIATED BY CHIRAL LEWIS-ACIDS [J].

CHAPUIS, C ;

JURCZAK, J .

HELVETICA CHIMICA ACTA, 1987, 70 (02) :436-440

[9] DEMONSTRATION OF THE SYNTHETIC POWER OF OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE DIELS-ALDER REACTIONS BY VERY EFFICIENT ROUTES TO CASSIOL AND GIBBERELLIC-ACID [J].

COREY, EJ ;

GUZMANPEREZ, A ;

LOH, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3611-3612

[10] 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

← 1 2 3 4 →