ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY STABLE AND EASILY PREPARED CAB CATALYSTS

被引：52

作者：

GAO, QZ ^{[1
]}

ISHIHARA, K ^{[1
]}

MARUYAMA, T ^{[1
]}

MOURI, M ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH ENGN,NAGOYA,AICHI 46401,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 04期

关键词：

D O I：

10.1016/S0040-4020(01)80812-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stable chiral (acyloxy)borane (CAB) complex is prepared in situ by mixing a tartaric acid derivative and arylboronic acids at room temperature. A solution of the catalyst is effective in catalyzing hetero Diels-Alder reactions to produce dihydropyrone derivatives of high optical purities.

引用

页码：979 / 988

页数：10

共 29 条

[1] INTERACTIVITY OF CHIRAL CATALYSTS AND CHIRAL AUXILIARIES IN THE CYCLOADDITION OF ACTIVATED DIENES WITH ALDEHYDES - A SYNTHESIS OF L-GLUCOSE
BEDNARSKI, M
DANISHEFSKY, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7060 - 7067
[2] Boger D. L., 1987, HETERO DIELS ALDER M
[3] 1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS
COREY, EJ
LOH, TP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) : 8966 - 8967
[4] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE
COREY, EJ
CYWIN, CL
ROPER, TD
[J]. TETRAHEDRON LETTERS, 1992, 33 (46) : 6907 - 6910
[5] THE ORIGIN OF GREATER THAN 200/1 ENANTIOSELECTIVITY IN A CATALYTIC DIELS-ALDER REACTION AS REVEALED BY PHYSICAL AND CHEMICAL STUDIES
COREY, EJ
LOH, TP
ROPER, TD
AZIMIOARA, MD
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8290 - 8292
[6] ON THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF SILYLOXY DIENES WITH ALPHA,BETA-UNSATURATED ALDEHYDES
DANISHEFSKY, S
KERWIN, JF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) : 3183 - 3184
[7] A FULLY SYNTHETIC ROUTE TO HIKOSAMINE
DANISHEFSKY, S
MARING, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) : 7762 - 7764
[8] DERIVATIVES OF 1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE FOR DIELS-ALDER REACTIONS
DANISHEFSKY, S
YAN, CF
SINGH, RK
GAMMILL, RB
MCCURRY, PM
FRITSCH, N
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) : 7001 - 7008
[9] CHIRAL (ACYLOXY)BORANE (CAB) - A POWERFUL AND PRACTICAL CATALYST FOR ASYMMETRIC DIELS-ALDER REACTIONS
FURUTA, K
SHIMIZU, S
MIWA, Y
YAMAMOTO, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1481 - 1483
[10] FURUTA K, 1991, SYNLETT, P439

← 1 2 3 →