Chiral titanium complexes. Synthesis of optically active unsaturated alcohols, diols, polypropionates and their use in the synthesis of biologically active compounds

被引：35

作者：

Cossy, J ^{[1
]}

Bouzbouz, S ^{[1
]}

Pradaux, F ^{[1
]}

Willis, C ^{[1
]}

Bellosta, V ^{[1
]}

机构：

[1] ESPCI, CNRS, Lab Chim Organ Associe, F-75231 Paris 05, France

来源：

SYNLETT | 2002年 / 10期

关键词：

allyltitanation; crotyltitanation; enantioselectivity; diols; polypropionates; natural products;

D O I：

10.1055/s-2002-34233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure allyltitanium and crotyltitanium complexes allow the enantioselective synthesis of 1,2-, 1,3- and 1,5-diols as well as polypropionate units. These complexes can be used in the synthesis of a great number of biologically active compounds.

引用

页码：1595 / 1606

页数：12

共 114 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] SYNTHESIS OF OPTICALLY-ACTIVE T-BUTYL (3R,5S)-3,5-ISOPROPYLIDENEDIOXY-6-HEPTYNOATE THROUGH BAKERS-YEAST REDUCTION OF METHYL 3-OXO-4-PENTYNOATE [J].

ANSARI, MH ;

KUSUMOTO, T ;

HIYAMA, T .

TETRAHEDRON LETTERS, 1993, 34 (51) :8271-8274

[3] 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

[4] Total synthesis of fostriecin (CI-920) [J].

Boger, DL ;

Ichikawa, S ;

Zhong, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4161-4167

[5] Synthesis of aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity via palladium-catalyzed heteroannulation of chiral arylpropargylic alcohols [J].

Botta, M ;

Summa, V ;

Corelli, F ;

DiPietro, G ;

Lombardi, P .

TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1263-1266

[6] Enantioselective synthesis of propargylic alcohols by addition of enantiopure cyclopentadienyldialkoxyallyltitanium complexes to acetylenic aldehydes [J].

BouzBouz, S ;

Pradaux, F ;

Cossy, J ;

Ferroud, C ;

Falguières, A .

TETRAHEDRON LETTERS, 2000, 41 (46) :8877-8880

[7] Efficient strategy for the synthesis of stereopentad subunits of scytophycin, rifamycin S, and discodermolide [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2001, 3 (25) :3995-3998

[8] Enantioselective allyltitanation. Efficient synthesis of the C1-C14 polyol subunit of amphotericin B [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2000, 2 (25) :3975-3977

[9] Enantioselective allyltitanation. Application to the synthesis of lactone units related to compactin and mevinolin [J].

Bouzbouz, S ;

Cossy, J .

TETRAHEDRON LETTERS, 2000, 41 (18) :3363-3366

[10] Enantioselective synthesis of syn- and anti-1,3-diols via allyltitanation of unprotected β-hydroxyaldehydes [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2000, 2 (04) :501-504

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