A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions

被引：661

作者：

Corey, EJ ^{[1
]}

Xu, F ^{[1
]}

Noe, MC ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1997年 / 119卷 / 50期

关键词：

D O I：

10.1021/ja973174y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

引用

页码：12414 / 12415

页数：2

共 22 条

[1] Kinetic investigations provide additional evidence that an enzyme-like binding pocket is crucial for high enantioselectivity in the bis-cinchona alkaloid catalyzed asymmetric dihydroxylation of olefins
Corey, EJ
Noe, MC
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[2] A critical analysis of the mechanistic basis of enantioselectivity in the bis-cinchona alkaloid catalyzed dihydroxylation of olefins
Corey, EJ
Noe, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) : 11038 - 11053
[3] RIGID AND HIGHLY ENANTIOSELECTIVE CATALYST FOR THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE CLARIFIES THE ORIGIN OF ENANTIOSPECIFICITY
COREY, EJ
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) : 12579 - 12580
[4] Enantioselective total synthesis of ecteinascidin 743
Corey, EJ
Gin, DY
Kania, RS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) : 9202 - 9203
[5] THE ORIGIN OF HIGH ENANTIOSELECTIVITY IN THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE AND CINCHONA ALKALOID CATALYSTS
COREY, EJ
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3828 - 3829
[6] Improved enantioselective dihydroxylation of bishomoallylic alcohol derivatives using a mechanistically inspired bis-cinchona alkaloid catalyst
Corey, EJ
Noe, MC
Ting, AY
[J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1735 - 1738
[7] X-RAY CRYSTALLOGRAPHIC STUDIES PROVIDE ADDITIONAL EVIDENCE THAT AN ENZYME-LIKE BINDING POCKET IS CRUCIAL TO THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS BY OSO4-BIS-CINCHONA ALKALOID COMPLEXES
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NOE, MC
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[J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2861 - 2864
[8] Dehmlow E.V., 1993, PHASE TRANSFER CATAL
[9] EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS
DOLLING, UH
DAVIS, P
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) : 446 - 447
[10] EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .3. A KINETIC AND MECHANISTIC STUDY OF THE ENANTIOSELECTIVE PHASE-TRANSFER METHYLATION OF 6,7-DICHLORO-5-METHOXY-2-PHENYL-1-INDANONE
HUGHES, DL
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SCHOENEWALDT, EF
GRABOWSKI, EJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) : 4745 - 4752

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