Efficient asymmetric synthesis of 1-alk-2-yne-1,4-diols

被引:27
作者
Diez, RS
Adger, B
Carreira, EM
机构
[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
[2] Univ Burgos, Fac Ciencias, Area Quim Organ, Burgos 09001, Spain
[3] Synetix, Cambridge CB2 5JE, England
关键词
1,4-diols; asymmetric synthesis; optically active compounds;
D O I
10.1016/S0040-4020(02)00985-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe an expeditious process that provides ready access to symmetrical and unsymmetrical optically active bispropargylic 1,4-diols. The method employs the use of a recent method we have developed involving terminal acetylenes, Zn(OTf)(2), amine base, and N-methyl ephedrine. The 1,4-diol products should serve as useful building blocks for asymmetric synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8341 / 8344
页数:4
相关论文
共 30 条
[1]   Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B [J].
Amador, M ;
Ariza, X ;
Garcia, J ;
Ortiz, J .
TETRAHEDRON LETTERS, 2002, 43 (15) :2691-2694
[2]   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
[3]   Facile enantioselective synthesis of a key homoallylic alcohol building block for polyketide synthesis:: TiF4-BINOL catalyzed allylsilylation with allyl trimethylsilane [J].
Bode, JW ;
Gauthier, DR ;
Carreira, EM .
CHEMICAL COMMUNICATIONS, 2001, (24) :2560-2561
[4]   Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3611-3612
[5]   Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6410-6424
[6]   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
[7]   CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND [J].
BURK, MJ ;
MARTINEZ, JP ;
FEASTER, JE ;
COSFORD, N .
TETRAHEDRON, 1994, 50 (15) :4399-4428
[8]   CATALYTIC, ENANTIOSELECTIVE ACETONE ALDOL ADDITIONS WITH 2-METHOXYPROPENE [J].
CARREIRA, EM ;
LEE, W ;
SINGER, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3649-3650
[9]   A NEW SYNTHETIC ROUTE TO PROSTAGLANDINS [J].
COREY, EJ ;
NIIMURA, K ;
KONISHI, Y ;
HASHIMOTO, S ;
HAMADA, Y .
TETRAHEDRON LETTERS, 1986, 27 (20) :2199-2202
[10]  
Fässler R, 2002, ANGEW CHEM INT EDIT, V41, P3054, DOI 10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO