Asymmetric synthesis of 3,4-dihydrocoumarins by rhodium-catalyzed reaction of 3-(2-hydroxyphenyl)cyclobutanones

被引:217
作者
Matsuda, Takanori [1 ]
Shigeno, Masanori [1 ]
Murakami, Masahiro [1 ]
机构
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 61585, Japan
关键词
D O I
10.1021/ja075141g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3,4-Dihydrocoumarin derivatives were synthesized in a highly enantioselective manner from 3-(2-hydroxyphenyl)cyclobutanones through enantioselective carbon-carbon bond cleavage. A cascade reaction with electron-deficient alkenes introduced a carbon-carbon bond at the 5-position of the dihydrocoumarins.
引用
收藏
页码:12086 / +
页数:3
相关论文
共 32 条
[1]   Catalytic and highly efficient 1,4-addition of terminal alkynes to conjugated enones by [RuCl2(p-cymene)]2/pyrrolidine [J].
Chang, S ;
Na, Y ;
Choi, E ;
Kim, S .
ORGANIC LETTERS, 2001, 3 (13) :2089-2091
[2]   Catalytic asymmetric cyclocarbonylation of o-isopropenylphenols:: Enantioselective synthesis of six-membered ring lactones [J].
Dong, C ;
Alper, H .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5011-5014
[3]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[4]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[5]   Pd-catalyzed alkyl to aryl migration and cyclization: An efficient synthesis of fused polycycles via multiple C-H activation [J].
Huang, QH ;
Fazio, A ;
Dai, GX ;
Campo, MA ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7460-7461
[6]   Nickel-catalyzed coupling of allyl chlorides and enynes [J].
Ikeda, S ;
Suzuki, K ;
Odashima, K .
CHEMICAL COMMUNICATIONS, 2006, (04) :457-459
[7]  
JUN CH, 2005, CHEM LETT, V34, P1462
[8]   Rhodium-catalyzed rapid synthesis of substituted phenols from cyclobutenones and alkynes or alkenes via C-C bond cleavage [J].
Kondo, Teruyuki ;
Niimi, Masatsugu ;
Nomura, Masato ;
Wada, Kenji ;
Mitsudo, Take-aki .
TETRAHEDRON LETTERS, 2007, 48 (16) :2837-2839
[9]   6-CHLORO-2,3-DIHYDRO-4H-1-BENZOPYRAN CARBOXYLIC-ACIDS - SYNTHESIS, OPTICAL RESOLUTION AND ABSOLUTE-CONFIGURATION [J].
LOIODICE, F ;
LONGO, A ;
BIANCO, P ;
TORTORELLA, V .
TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :1001-1011
[10]   1,4-Migration of rhodium and palladium in catalytic organometallic reactions [J].
Ma, SM ;
Gu, ZH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (46) :7512-7517