Construction of optically active CF3-containing quaternary carbon centers via stereospecific SN2′ reaction

被引:63
作者
Kimura, M
Yamazaki, T
Kitazume, T
Kubota, T
机构
[1] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Midori Ku, Yokohama, Kanagawa 2268501, Japan
[2] Ibaraki Univ, Dept Mat Sci, Hitachi, Ibaraki 3168511, Japan
关键词
D O I
10.1021/ol0481941
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phosphates from 3-substituted 4,4,4-trifluorobut-2-en-1-ols were found to be effective for construction of CF3-containing quaternary carbon centers by way of Cu(l)-catalyzed Grignard reactions in the presence of catalytic amounts of CuCN and trimethylsilyl chloride (TMSCI) in an anti S(N)2' manner.
引用
收藏
页码:4651 / 4654
页数:4
相关论文
共 29 条
[1]  
BACKVALL JE, 1994, J ORG CHEM, V59, P4126
[2]  
BACKVALL JE, 1990, J AM CHEM SOC, V112, P6615
[3]   EFFECT OF TMSCL ON THE CONJUGATE ADDITION OF ORGANOCUPRATES TO ALPHA-ENONES - A NEW MECHANISM [J].
BERTZ, SH ;
MIAO, GB ;
ROSSITER, BE ;
SNYDER, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11023-11024
[4]   Total syntheses of (+)- and (-)-cacospongionolide B, cacospongionolide E, and related analogues.: Preliminary study of structural features required for phospholipase A2 inhibition [J].
Cheung, AK ;
Murelli, R ;
Snapper, ML .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5712-5719
[5]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[6]  
2-V
[7]   D-ORBITAL STEREOELECTRONIC CONTROL OF THE STEREOCHEMISTRY OF SN2' DISPLACEMENTS BY ORGANOCUPRATE REAGENTS [J].
COREY, EJ ;
BOAZ, NW .
TETRAHEDRON LETTERS, 1984, 25 (29) :3063-3066
[8]   Stereoselective formation of quaternary carbon centers and related functions [J].
Denissova, I ;
Barriault, L .
TETRAHEDRON, 2003, 59 (51) :10105-10146
[9]   ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].
FUJI, K .
CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066
[10]   Stereoselective synthesis of the ABC ring system of norzoanthamine [J].
Ghosh, S ;
Rivas, F ;
Fischer, D ;
González, MA ;
Theodorakis, EA .
ORGANIC LETTERS, 2004, 6 (06) :941-944