Efficient and stereocontrolled synthesis of polysubstituted tetrahydropyrans by an allylstannylation/Bi(III)-promoted cyclisation strategy

被引:41
作者
Leroy, B [1 ]
Markó, IE [1 ]
机构
[1] Univ Catholique Louvain, Dept Chim, B-1348 Louvain, Belgium
关键词
allylation; tin; cyclisation; Sakurai reactions; carbamate; bismuth;
D O I
10.1016/S0040-4039(01)01836-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel sequence, involving the condensation between a highly functionalised allylstannane and various aldehydes, followed by a bismuth triflate-promoted intramolecular Sakurai cyclisation (IMSC) of the resulting homoallylic alcohols, allows a rapid and stereocontrolled access to a range of polysubstituted tetrahydropyrans. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8685 / 8688
页数:4
相关论文
共 22 条
[2]   Radical allylations with trimethyl[2-[(tributylstannyl)methyl]-2-propenyl] silane or trimethy[2-[(triphenylstannyl)-methyl]-2-propenyl]silane [J].
Clive, DLJ ;
Paul, CC ;
Wang, ZR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7028-7032
[3]   Saturated oxygen heterocycles [J].
Elliott, MC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (09) :1291-1318
[4]  
FeneauDupont J, 1997, B SOC CHIM BELG, V106, P173
[5]  
Hoppe D, 1997, ANGEW CHEM INT EDIT, V36, P2283
[6]   METALATED NITROGEN DERIVATIVES OF CARBONIC-ACID IN ORGANIC-SYNTHESIS .28. THE HOMOALDOL REACTION, OR HOW TO OVERCOME PROBLEMS OF REGIO-SELECTIVITY AND STEREO-SELECTIVITY [J].
HOPPE, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (12) :932-948
[7]  
Kang KT, 1998, SYNLETT, P921
[8]   An efficient method for the preparation of bismuth(III) trifluoromethanesulfonate [J].
Labrouillère, M ;
Le Roux, C ;
Gaspard, H ;
Laporterie, A ;
Dubac, J ;
Desmurs, JR .
TETRAHEDRON LETTERS, 1999, 40 (02) :285-286
[9]  
Laurent-Robert H, 2000, SYNLETT, P1160
[10]  
Le Roux C, 1998, SYNLETT, P1249