Regio- and stereocontrol elements in Rh(II)-catalyzed intramolecular C-H insertion of α-diazo-α-(phenylsulfonyl)acetamides

被引:59
作者
Yoon, CH [1 ]
Zaworotko, MJ [1 ]
Moulton, B [1 ]
Jung, KW [1 ]
机构
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
关键词
D O I
10.1021/ol016647l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Intramolecular C-H insertion reaction of alpha -diazo-alpha-(phenylsulfonyl)aceta rn ides proceeded with high regio- and stereoselectivities to afford highly functionalized gamma -lactams predominantly or exclusively. The high regioselectivity was attributed to the use of the phenylsulfonyl moiety, which altered electron density at the carbenoid center and exerted a steric effect during the insertion reaction. Also described herein are three control elements to determine regioselectivity, which are amide conformational, stereoelectronic, and substituent effects.
引用
收藏
页码:3539 / 3542
页数:4
相关论文
共 34 条
[1]   Enantioselective synthesis of 4-substituted 2-pyrrolidinones by site-selective C-H insertion of α-methoxycarbonyl-α-diazoacetanilides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] [J].
Anada, M ;
Hashimoto, S .
TETRAHEDRON LETTERS, 1998, 39 (1-2) :79-82
[2]   INTRAMOLECULAR RHODIUM CARBENOID INSERTIONS INTO AROMATIC C-H BONDS - PREPARATION OF 1,3-DIHYDROTHIOPHENE 2,2-DIOXIDES FUSED ONTO AROMATIC RINGS [J].
BABU, SD ;
HRYTSAK, MD ;
DURST, T .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (06) :1071-1076
[3]  
BARROW KD, 1988, TETRAHEDRON LETT, V29, P2283
[4]   A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES [J].
BURGESS, LE ;
MEYERS, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1656-1662
[5]   Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity [J].
Davies, HML ;
Panaro, SA .
TETRAHEDRON, 2000, 56 (28) :4871-4880
[6]   THE RHODIUM CARBENOID ROUTE TO CYCLIC ETHERS - SYNTHESIS OF THE CIS-2,7-DISUBSTITUTED OXEPANE SKELETON OF ISOLAUREPINNACIN [J].
DAVIES, MJ ;
MOODY, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :9-12
[7]  
DICOSIMO R, 1998, J ORG CHEM, V63, P4792
[8]   Stereoselective synthesis of 4-alkylidene pyrrolidinones and pyrrolizidinones [J].
Dieter, RK ;
Lu, K .
TETRAHEDRON LETTERS, 1999, 40 (21) :4011-4014
[9]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[10]   SYNTHESIS OF NITROGEN-CONTAINING POLYCYCLES VIA RHODIUM(II)-INDUCED CYCLIZATION CYCLOADDITION AND INSERTION REACTIONS OF N-(DIAZOACETOACETYL)AMIDES - CONFORMATIONAL CONTROL OF REACTION SELECTIVITY [J].
DOYLE, MP ;
PIETERS, RJ ;
TAUNTON, J ;
PHO, HQ ;
PADWA, A ;
HERTZOG, DL ;
PRECEDO, L .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :820-829