Cumyl:: A better N-protecting group of α-diazo acetamides for intra-molecular C-H insertion reaction and its application in the synthesis of pregabalin and 3-benzyloxy pyrrolidine

被引:25
作者
Chen, ZL
Chen, ZY
Jiang, YZ
Hu, WH [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth Chirotechnol Sichuan Provi, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Aymmetr Synth, Chengdu 610041, Peoples R China
关键词
cumyl; C-H insertion; pregabalin; pyrrolidine;
D O I
10.1055/s-2004-829568
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Via intramolecular C-H insertion of N-cumyl alpha-diazo acetamides, gamma-lactams were efficiently synthesized with excellent regioselectivity. A concise route for the preparation of pregabalin (79% overall yield) and 3-benzyloxy pyrrolidine (21% overall yield) were reported.
引用
收藏
页码:1763 / 1764
页数:2
相关论文
共 17 条
[1]  
Anada M, 1999, SYNLETT, P1775
[2]   Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization [J].
Clayden, J ;
Menet, CJ ;
Tchabanenko, K .
TETRAHEDRON, 2002, 58 (23) :4727-4733
[3]   Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].
Davies, HML ;
Beckwith, REJ .
CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903
[4]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[5]   Influences of catalyst configuration and catalyst loading on selectivities in reactions of diazoacetamides. Barrier to equilibrium between diastereomeric conformations [J].
Doyle, MP ;
Hu, WH ;
Wee, AGH ;
Wang, ZY ;
Duncan, SC .
ORGANIC LETTERS, 2003, 5 (04) :407-410
[6]  
DOYLE MP, 1998, MODERN CATALYTIC MET, P129
[7]  
Merlic CA, 2003, SYNTHESIS-STUTTGART, P1137
[8]   CONTROL OF CHEMOSELECTIVITY IN CATALYTIC CARBENOID REACTIONS - DIRHODIUM(II) LIGAND EFFECTS ON RELATIVE REACTIVITIES [J].
PADWA, A ;
AUSTIN, DJ ;
HORNBUCKLE, SF ;
SEMONES, MA ;
DOYLE, MP ;
PROTOPOPOVA, MN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1874-1876
[9]   LIGAND EFFECTS ON DIRHODIUM(II) CARBENE REACTIVITIES - HIGHLY EFFECTIVE SWITCHING BETWEEN COMPETITIVE CARBENOID TRANSFORMATIONS [J].
PADWA, A ;
AUSTIN, DJ ;
PRICE, AT ;
SEMONES, MA ;
DOYLE, MP ;
PROTOPOPOVA, MN ;
WINCHESTER, WR ;
TRAN, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8669-8680
[10]  
WATANABE N, 1994, SYNLETT, P1031