Highly enantioselective alkynylzinc addition to aromatic aldehydes catalyzed by self-assembled titanium catalysts

被引：169

作者：

Li, XS

Lu, G

Kwok, WH

Chan, ASC ^{[1
]}

机构：

[1] Hong Kong Polytech Univ, Inst Mol Technol Drug Discovery & Synth, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 43期

关键词：

D O I：

10.1021/ja025541y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective catalyst generated by a combination of BINOL and another ligand with Ti(OiPr)4 was found to be highly effective for the alkynylzinc addition to aromatic aldehydes with enantioselectivities as high as >99%. Copyright © 2002 American Chemical Society.

引用

页码：12636 / 12637

页数：2

共 28 条

[1] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].

Anand, NK ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688

[2] Highly enantioenriched propargylic alcohols by oxazaborolidine-mediated reduction of acetylenic ketones [J].

Bach, J ;

Berenguer, R ;

Garcia, J ;

Loscertales, T ;

Vilarrasa, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9021-9025

[3] Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].

Boyall, D ;

López, F ;

Sasaki, H ;

Frantz, D ;

Carreira, EM .

ORGANIC LETTERS, 2000, 2 (26) :4233-4236

[4]

CHAN AS, 1997, J AM CHEM SOC, V119, P4980

[5] An efficient catalytic stereoselective route to a key intermediate for the synthesis of the long-lived PGI(2) analog ZK 96480 (Cicaprost(TM)) [J].

Corey, EJ ;

Helal, CJ .

TETRAHEDRON LETTERS, 1997, 38 (43) :7511-7514

[6] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES [J].

COREY, EJ ;

HELAL, CJ .

TETRAHEDRON LETTERS, 1995, 36 (50) :9153-9156

[7] Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes [J].

Frantz, DE ;

Fässler, R ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1806-1807

[8] The discovery of novel reactivity in the development of C-C bond-forming reactions:: In situ generation of zinc acetylides with ZnII/R3N [J].

Frantz, DE ;

Fässler, R ;

Tomooka, CS ;

Carreira, EM .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :373-381

[9]

HELAL CJ, 1996, J AM CHEM SOC, V118, P19038

[10] EFFICIENT LIGANDS, CHIRAL 2-[2,2-DIMETHYL-1-(2-PYRIDYL)PROPOXY]-1,1-DIARYLETHANOLS FOR HIGHLY ENANTIOSELECTIVE ADDITION OF ALKYNYLZINC REAGENTS TO VARIOUS ALDEHYDES [J].

ISHIZAKI, M ;

HOSHINO, O .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1901-1904

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