Three-component, stereoselective palladium-catalyzed synthesis of functionalized bicyclopentanoids

被引:8
作者
Hulin, B [1 ]
Newton, LS [1 ]
Cabral, S [1 ]
Walker, AJ [1 ]
Bordner, J [1 ]
机构
[1] Pfizer Global Res & Dev, Groton, CT 06340 USA
关键词
D O I
10.1021/ol048140r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,5-Cyclooctadiene can be stereoselectively transformed into a substituted bicyclo[3.3.0]octane ring system under palladium catalysis with concomitant formation of three carbon-carbon bonds. Reaction with an aryl iodide or triflate and malonate gives an exo-endo product, while the reaction with a malonate in the presence of oxygen affords a bis-endo adduct.
引用
收藏
页码:4343 / 4345
页数:3
相关论文
共 33 条
[31]   SELECTIVITIES IN ORGANIC-REACTIONS VIA PI-ALLYLPALLADIUM COMPLEXES [J].
TSUJI, J .
PURE AND APPLIED CHEMISTRY, 1989, 61 (10) :1673-1680
[32]   XANTHATE TRANSFER ADDITION OF A GLYCINE RADICAL EQUIVALENT TO ALKENES - A NOVEL ROUTE TO ALPHA-AMINO-ACID DERIVATIVES [J].
UDDING, JH ;
HIEMSTRA, H ;
SPECKAMP, WN .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3721-3725
[33]   Base-free oxidative homocoupling of arylboronic esters [J].
Yoshida, H ;
Yamaryo, Y ;
Ohshita, J ;
Kunai, A .
TETRAHEDRON LETTERS, 2003, 44 (08) :1541-1544