Highly diastereoselective conjugate addition of aryllithium to chiral β-nitrostyrene derivative:: An application to the asymmetric synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline

被引:5
作者
Asami, Masatoshi [1 ]
Taketoshi, Ayako [1 ]
Miyoshi, Keita [1 ]
Hoshino, Hayato [1 ]
Sakakibara, Kazuhisa [1 ]
机构
[1] Yokohama Natl Univ, Grad Sch Engn, Dept Adv Mat Chem, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan
关键词
D O I
10.1246/cl.2007.64
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly diastereoselective conjugate addition of aryllithium to beta-nitrostyrene derivative, having chiral acetal moiety derived from (S,S)- 1,2-bis(1-hydroxypropyl)benzene, was achieved. The adduct was transformed to 4-aryl-1,2,3,4-tetrahydroisoquinoline in high enantiomeric excess (ee).
引用
收藏
页码:64 / 65
页数:2
相关论文
共 18 条
[1]   MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].
ALLINGER, NL ;
YUH, YH ;
LII, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566
[2]   Investigation of the asymmetric ionic Diels-Alder reaction for the synthesis of cis-decalins [J].
Anderson, JC ;
Blake, AJ ;
Graham, JP ;
Wilson, C .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (16) :2877-2885
[3]  
Asami M, 2001, CHEM LETT, P1110
[4]   Syntheses and applications of C2-symmetric chiral diols [J].
Bhowmick, Kartick C. ;
Joshi, Navalkishore N. .
TETRAHEDRON-ASYMMETRY, 2006, 17 (13) :1901-1929
[5]   Asymmetric synthesis of (+)- and (-)-latifine [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P ;
Lebrun, S .
TETRAHEDRON-ASYMMETRY, 2003, 14 (10) :1309-1316
[6]  
Fujioka H., 1994, STUDIES NATURAL PROD, V14, P469, DOI [10.1016/b978-0-444-81780-8.50018-1, DOI 10.1016/B978-0-444-81780-8.50018-1]
[7]   1,4-di-O-tert-alkyl-L-threitols as chiral auxiliaries in the asymmetric nucleophilic addition of alkyllithiums to hydrazones [J].
Hsieh, YT ;
Lee, GH ;
Wang, Y ;
Luh, TY .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1484-1490
[8]   STEREOSELECTIVE REDUCTION OF ACETALS - A METHOD FOR REDUCTIVE GENERATION OF HETEROCYCLIC RING-SYSTEMS [J].
ISHIHARA, K ;
MORI, A ;
YAMAMOTO, H .
TETRAHEDRON, 1990, 46 (13-14) :4595-4612
[9]   ASYMMETRIC-SYNTHESIS OF BETA-ALKOXYCYCLIC ETHERS VIA THE INTRAMOLECULAR CYCLIZATION OF GROUP-14 ALLYLS CONTAINING CHIRAL ACETALS [J].
KADOTA, I ;
MIURA, K ;
YAMAMOTO, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (17) :1953-1954
[10]  
KIHARA M, 1995, CHEM PHARM BULL, V43, P1543