A [3+3] annelation approach to tetrahydropyridines

被引:44
作者
Pattenden, Lisa C.
Wybrow, Robert A. J.
Smith, Stephen A.
Harrity, Joseph P. A.
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] GlaxoSmithKline Res & Dev Ltd, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1021/ol0610789
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A stepwise [3+3] annelation sequence to tetrahydropyridines via addition of the BUchi Grignard to aziridines has been developed. These intermediates can be further functionalized with good regio- and stereocontrol and this methodology has been employed in the stereoselective formal synthesis of (-)-dihydropinidine.
引用
收藏
页码:3089 / 3091
页数:3
相关论文
共 25 条
[1]   1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis: Stereoselective homo- and hetero-Diels-Alder reactions [J].
Adelbrecht, JC ;
Craig, D ;
Fleming, AJ ;
Martin, FM .
SYNLETT, 2005, (17) :2643-2647
[2]   1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis.: Regio- and stereoselective SN1 reactions [J].
Adelbrecht, JC ;
Craig, D ;
Thorimbert, S .
TETRAHEDRON LETTERS, 2001, 42 (47) :8369-8372
[3]  
Adelbrecht JC, 2000, SYNLETT, P467
[4]   C-glycosides to fused polycyclic ethers [J].
Allwein, SP ;
Cox, JM ;
Howard, BE ;
Johnson, HWB ;
Rainier, JD .
TETRAHEDRON, 2002, 58 (10) :1997-2009
[5]   Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam [J].
Amat, M ;
Llor, N ;
Hidalgo, J ;
Escolano, C ;
Bosch, J .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1919-1928
[6]   DEFENSE-MECHANISMS OF ANTHROPODS .119. ALKALOIDS OF THE MEXICAN BEAN BEETLE, EPILACHNA-VARIVESTIS (COCCINELLIDAE) [J].
ATTYGALLE, AB ;
XU, SC ;
MCCORMICK, KD ;
MEINWALD, J ;
BLANKESPOOR, CL ;
EISNER, T .
TETRAHEDRON, 1993, 49 (41) :9333-9342
[7]  
BUCHI G, 1969, J ORG CHEM, V34, P1122
[8]  
Craig D, 1998, SYNLETT, P58
[9]   1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis.: Highly regio- and stereoselective SN1′ and alkylation reactions [J].
Craig, D ;
McCague, R ;
Potter, GA ;
Williams, MRV .
SYNLETT, 1998, (01) :55-+
[10]   Development of a stepwise [3+3] annelation to functionalized piperidines [J].
Goodenough, KM ;
Raubo, P ;
Harrity, JPA .
ORGANIC LETTERS, 2005, 7 (14) :2993-2996