ENE REACTION OF 2-(ALKYLTHIO)ALLYL SILYL ETHER INVOLVING A CHIRALITY TRANSFER

被引:24
作者
TANINO, K [1 ]
SHODA, H [1 ]
NAKAMURA, T [1 ]
KUWAJIMA, I [1 ]
机构
[1] TOKYO INST TECHNOL,DEPT CHEM,TOKYO 152,JAPAN
关键词
D O I
10.1016/S0040-4039(00)91616-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly enantio-selective ene reaction was developed on the bases of chirality transfer. Under the influence of Me2AlCl, the reactions of various aldehydes with (S)-3-(tert-butyldimethylsiloxy)-2-(ethylthio)-1-butene which was easily prepared from (S)-ethyl lactate afforded the optically active adducts in high ee.
引用
收藏
页码:1337 / 1340
页数:4
相关论文
共 17 条
[1]  
ADACHI A, IN PRESS
[2]  
BOGER DL, 1987, HETERO DIELSALDER ME, P167
[3]   METHOD FOR PROTECTION OF LACTONES AND ESTERS AGAINST NUCLEOPHILIC ATTACK [J].
COREY, EJ ;
BEAMES, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) :5829-5831
[4]   (+)-1(S),5(R),8(S)-8-PHENYL-2-AZABICYCLO[3.3.0]OCTAN-8-OL N,O-METHYLBORONATE (2) AND ITS ENANTIOMER, CHIRAL CHEMZYMES WHICH SERVE AS CATALYSTS FOR THEIR OWN ENANTIOSELECTIVE SYNTHESIS [J].
COREY, EJ ;
CHEN, CP ;
REICHARD, GA .
TETRAHEDRON LETTERS, 1989, 30 (41) :5547-5550
[5]   ENE AND RETRO-ENE REACTIONS IN GROUP-14 ORGANOMETALLIC CHEMISTRY [J].
DUBAC, J ;
LAPORTERIE, A .
CHEMICAL REVIEWS, 1987, 87 (02) :319-334
[6]   PREPARATION OF TERT-BUTYL THIOESTERS [J].
HATCH, RP ;
WEINREB, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3960-3961
[7]  
Hill R. K., 1984, ASYMMETRIC SYNTHESIS, V3, P503
[8]   STEREOCHEMISTRY OF NO-MECHANISM REACTIONS - TRANSFER OF ASYMMETRY IN REACTION OF OLEFINS WITH DIENOPHILES [J].
HILL, RK ;
RABINOVICZ, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (05) :965-&
[9]   ENE REACTION [J].
HOFFMANN, HM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :556-&
[10]  
HOUK RJ, 1987, J AM CHEM SOC, V109, P6947