Enantioselective scandium-catalyzed vinylsilane additions:: A new approach to the synthesis of enantiopure β,γ-unsaturated α-hydroxy acid derivatives

被引:37
作者
Evans, David A. [1 ]
Aye, Yimon [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ja063878k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of the Lewis acid-catalyzed alkenylation using trimethylvinylsilanes is described. Both aliphatic and aromatic vinylsilanes were effective nucleophiles at room temperature affording chiral allylic alcohol products in excellent enantioselectivities (97 → 99% ee) and in moderate to good yields (45-99%). Complete retention of vinysilane geometry was observed where applicable. Copyright © 2006 American Chemical Society.
引用
收藏
页码:11034 / 11035
页数:2
相关论文
共 14 条
[1]  
Cain D., 1979, Carbon-Carbon Bond Formation, V1, P85
[2]   SILICON IN SYNTHESIS .8. VINYLTRIMETHYLSILANE, A CONVENIENT ETHYLENE EQUIVALENT FOR THE SYNTHESIS OF VINYL ARYL SULFIDES, VINYL ARYL SULFOXIDES, THIOSILYLKETENE ACETALS, AND FUSED CYCLOPENTENONES [J].
COOKE, F ;
MOERCK, R ;
SCHWINDEMAN, J ;
MAGNUS, P .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1046-1053
[3]  
CORRIU RJP, 2003, CHEM ORGANIC SILICON, P1241
[4]   Asymmetric, anti-selective scandium-catalyzed Sakurai additions to glyoxyamide.: Applications to the syntheses of N-Boc D-alloisoleucine and D-isoleucine [J].
Evans, DA ;
Aye, Y ;
Wu, J .
ORGANIC LETTERS, 2006, 8 (10) :2071-2073
[5]   Enantioselective Syn-selective scandium-catalyzed ene reactions [J].
Evans, DA ;
Wu, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8006-8007
[6]  
Fleming I., 1989, ORG REACTIONS, V37, P57
[7]   HYDROZIRCONATION .3. STEREOSPECIFIC AND REGIOSELECTIVE FUNCTIONALIZATION OF ALKYLACETYLENES VIA VINYLZIRCONIUM(IV) INTERMEDIATES [J].
HART, DW ;
BLACKBURN, TF ;
SCHWARTZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :679-680
[8]   Tetraalkylammonium salt-based catalyst systems for directing the arylation of vinyltrimethylsilane [J].
Jeffery, T .
TETRAHEDRON LETTERS, 1999, 40 (09) :1673-1676
[9]   SYNTHESIS OF VINYL SILANES FROM VINYL SILANE PHOSPHATES [J].
KOERWITZ, FL ;
HAMMOND, GB ;
WIEMER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :743-747
[10]  
Luh T.- Y., 2003, CHEM ORGANIC SILICON, P1793