The application of the formyl C-H--O hydrogen bond postulate to the understanding of enantioselective reactions involving chiral boron Lewis acids and aldehydes

被引：98

作者：

Corey, EJ

Rohde, JJ

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 01期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(96)02249-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of noteworthy enantioselective reactions involving a variety of chiral boron Lewis acids and aldehydes can be rationalized in terms of the occurrence of formyl CH-O hydrogen bonds in the transition states and the additional three-dimensional organization which they provide. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：37 / 40

页数：4

相关论文

共 10 条

[1] 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

[2] 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

[3] 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

[4] ACYLOXYBORANE - AN ACTIVATING DEVICE FOR CARBOXYLIC-ACIDS [J].

FURUTA, K ;

MIWA, Y ;

IWANAGA, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6254-6255

[5] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY STABLE AND EASILY PREPARED CAB CATALYSTS [J].

GAO, QZ ;

MARUYAMA, T ;

MOURI, M ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1951-1952

[6]

HASHIMOTO S, 1970, J CHEM SOC CHEM COMM, P437

[7] A novel chiral super-Lewis acidic catalyst for enantioselective synthesis [J].

Hayashi, Y ;

Rohde, JJ ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) :5502-5503

[8] MECHANISTIC STUDIES OF A CAB-CATALYZED ASYMMETRIC DIELS-ALDER REACTION [J].

ISHIHARA, K ;

GAO, QZ ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10412-10413

[9] N,N'-DIBENZYL-N,N'-ETHYLENETARTRAMIDE - A RATIONALLY DESIGNED CHIRAL AUXILIARY FOR THE ALLYLBORATION REACTION [J].

ROUSH, WR ;

BANFI, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :3979-3982

[10] STEREOCHEMICAL ASPECTS OF ASYMMETRIC DIELS-ALDER REACTION CATALYZED BY CHIRAL ALKOXYALUMINUM DICHLORIDES [J].

TAKEMURA, H ;

KOMESHIMA, N ;

TAKAHASHI, I ;

HASHIMOTO, S ;

IKOTA, N ;

TOMIOKA, K ;

KOGA, K .

TETRAHEDRON LETTERS, 1987, 28 (46) :5687-5690