CATALYTIC ASYMMETRIC ALLYLATION USING A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS-ACID CATALYST

被引：167

作者：

ISHIHARA, K ^{[1
]}

MOURI, M ^{[1
]}

GAO, QZ ^{[1
]}

MARUYAMA, T ^{[1
]}

FURUTA, K ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA 46401,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 24期

关键词：

D O I：

10.1021/ja00077a054

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.

引用

收藏

页码：11490 / 11495

页数：6

相关论文

共 30 条

[1] PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES [J].

ANDREINI, BP ;

CARPITA, A ;

ROSSI, R ;

SCAMUZZI, B .

TETRAHEDRON, 1989, 45 (17) :5621-5640

[2] SYNTHESIS OF ENANTIOMERICALLY ENRICHED HOMOALLYLIC ALCOHOLS AND OF 1,2-DIEN-4-OLS USING CHIRAL TIN(IV) COMPLEXES CONTAINING DIETHYL TARTRATE AS AN AUXILIARY LIGAND [J].

BOLDRINI, GP ;

LODI, L ;

TAGLIAVINI, E ;

TARASCO, C ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5447-5452

[3] STUDIES ON TRIFLUOROACETIC ACID .1. TRIFLUOROACETIC ANHYDRIDE AS A PROMOTER OF ESTER FORMATION BETWEEN HYDROXY-COMPOUNDS AND CARBOXYLIC ACIDS [J].

BOURNE, EJ ;

STACEY, M ;

TATLOW, JC ;

TEDDER, JM .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (NOV) :2976-2979

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].

BROWN, HC ;

RANDAD, RS ;

BHAT, KS ;

ZAIDLEWICZ, M ;

RACHERLA, US .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392

[5] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES [J].

COREY, EJ ;

YU, CM ;

KIM, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5495-5496

[6] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

COSTA, AL ;

PIAZZA, MG ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002

[7] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALDOL REACTIONS VIA ALPHA-SILYL KETONES, ASYMMETRIC-SYNTHESIS OF THE AGGREGATION PHEROMONE SITOPHILURE [J].

ENDERS, D ;

LOHRAY, BB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (04) :581-583

[8] ENANTIOSELECTIVE SYNTHESES OF SECONDARY HOMOALLYL ALCOHOLS WITH OPTICALLY-ACTIVE ETA-3-ALLYLMOLYBDENUM COMPLEXES [J].

FALLER, JW ;

LINEBARRIER, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1937-1939

[9]

Fleming I., 1989, ORG REACTIONS, V37, P57

[10] CHIRAL (ACYLOXY)BORANE (CAB) - A POWERFUL AND PRACTICAL CATALYST FOR ASYMMETRIC DIELS-ALDER REACTIONS [J].

FURUTA, K ;

SHIMIZU, S ;

MIWA, Y ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1481-1483