Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes:: crucial role of the stoichiometry of the Lewis acid

被引：22

作者：

Dubost, C

Leroy, B

Markó, IE

Tinant, B

Declercq, JP

Bryans, J

机构：

[1] Univ Catholique Louvain, Dept Chim, Unite Chim Organ & Med, B-1348 Louvain, Belgium

[2] Univ Catholique Louvain, Dept Chim, Unite Chim Struct, B-1348 Louvain, Belgium

[3] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON | 2004年 / 60卷 / 35期

关键词：

allylation; allylstannane; chelation; triols; stereocontrol; Lewis acid;

D O I：

10.1016/j.tet.2004.06.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure syn-anti and syn-syn configured triol units are efficiently synthesized by the SnCl4 mediated allylation of chiral alpha-benzyloxyaldehydes with the uniquely functionalised allylstannane 9. Remarkably, the stereochemistry of the adducts is solely governed by the amount of Lewis acid employed. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7693 / 7704

页数：12

相关论文

共 41 条

[1] Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation [J].

Allevi, P ;

Tarocco, G ;

Longo, A ;

Anastasia, M ;

Cajone, F .

TETRAHEDRON-ASYMMETRY, 1997, 8 (08) :1315-1325

[2]

Batey RA, 2000, SYNTHESIS-STUTTGART, P990

[3] AN ASYMMETRIC-SYNTHESIS OF D-1,6-DIEPICASTANOSPERMINE [J].

BURGESS, K ;

CHAPLIN, DA .

TETRAHEDRON LETTERS, 1992, 33 (41) :6077-6080

[4] 1,6-ASYMMETRIC INDUCTION IN LEWIS-ACID PROMOTED REACTIONS OF EPSILON-METHOXY-ALLYLSTANNANES AND EPSILON-HYDROXY-ALLYLSTANNANES AND ALDEHYDES [J].

CAREY, JS ;

THOMAS, EJ .

TETRAHEDRON LETTERS, 1993, 34 (24) :3935-3938

[5] STEREOCHEMICAL STUDIES ON BORONOLIDE, AN ALPHA-PYRONE FROM TETRADENIA-BARBERAE [J].

DAVIESCOLEMAN, MT ;

RIVETT, DEA .

PHYTOCHEMISTRY, 1987, 26 (11) :3047-3050

[6] High 1,4-syn-induction in the addition of chiral allyltrichlorostannanes to chiral aldehydes [J].

Dias, LC ;

Giacomini, R ;

Meira, PRR ;

Ferreira, E ;

Ferreira, AA ;

Diaz, G ;

dos Santos, DR ;

Steil, LJ .

ARKIVOC, 2003, :240-261

[7] Allyltrichlorostannane additions to chiral aldehydes [J].

Dias, LC ;

dos Santos, DR ;

Steil, LJ .

TETRAHEDRON LETTERS, 2003, 44 (36) :6861-6866

[8] NMR study on ligand exchange reaction between a chiral allylsilane and SnCl4 [J].

Dias, LC ;

Meira, PRR ;

Ferreira, E .

ORGANIC LETTERS, 1999, 1 (09) :1335-1338

[9] On 1,4-diastereoselectivity in the chiral allylsilane addition to chiral α-substituted aldehydes [J].

Dias, LC ;

Giacomini, R .

TETRAHEDRON LETTERS, 1998, 39 (30) :5343-5346

[10] IDENTIFICATION OF LICHEN SUBSTANCES BY A STANDARDIZED HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC METHOD [J].

FEIGE, GB ;

LUMBSCH, HT ;

HUNECK, S ;

ELIX, JA .

JOURNAL OF CHROMATOGRAPHY, 1993, 646 (02) :417-427

← 1 2 3 4 5 →