Asymmetric carbonyl addition reactions to benzyloxyaldehydes by binaphthol-titanium catalyst: Anti- vs. syn-diastereofacial preference in anomalous nonchelation complexation

被引：20

作者：

Mikami, K ^{[1
]}

Matsukawa, S ^{[1
]}

Sawa, E ^{[1
]}

Harada, A ^{[1
]}

Koga, N ^{[1
]}

机构：

[1] NAGOYA UNIV,COLL GEN EDUC,DEPT CHEM,NAGOYA,AICHI 464,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(97)00231-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An anomalous nonchelation diastereofacial selectivity is observed in the titanium-catalyzed carbonyl addition reaction to benzyl-protected alkoxyaldehydes. There is a dichotomy in the sense of syn- vs. anti-diastereofacial preference, dictated by the bulkiness of the migratory group: The sterically demanding silyl group gives syn-diastereofacial preference and the less sterically demanding proton lends to anti-diastereofacial preference. (C) 1997 Elsevier Science Ltd.

引用

页码：1951 / 1954

页数：4

共 39 条

[1]

ANH NT, 1977, NOUV J CHIM, V1, P61

[2]

[Anonymous], 1992, Org. Synth

[3] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV) [J].

CARREIRA, EM ;

SINGER, RA ;

LEE, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8837-8838

[4]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[5] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[6] SYNTHESIS, STRUCTURE, AND REACTIVITY OF AN ORGANOGERMANIUM LEWIS ACID [J].

DENMARK, SE ;

JACOBS, RT ;

DAIHO, G ;

WILSON, S .

ORGANOMETALLICS, 1990, 9 (12) :3015-3019

[7] CHEMISTRY OF ENOXYSILACYCLOBUTANES - HIGHLY SELECTIVE UNCATALYZED ALDOL ADDITIONS [J].

DENMARK, SE ;

GRIEDEL, BD ;

COE, DM ;

SCHNUTE, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7026-7043

[8] THE CHEMISTRY OF ENOXYSILACYCLOBUTANES - HIGHLY SELECTIVE, UNCATALYZED ALDOL ADDITIONS [J].

DENMARK, SE ;

GRIEDEL, BD ;

COE, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :988-990

[9] CHIRAL TITANIUM COMPLEXES FOR ENANTIOSELECTIVE ADDITION OF NUCLEOPHILES TO CARBONYL GROUPS [J].

DUTHALER, RO ;

HAFNER, A .

CHEMICAL REVIEWS, 1992, 92 (05) :807-832

[10] CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST [J].

FURUTA, K ;

MARUYAMA, T ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1041-1042

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