AMIDE-BASED PROTECTING/RADICAL TRANSLOCATING (PRT) GROUPS - GENERATION OF RADICALS ADJACENT TO CARBONYLS BY 1,5-HYDROGEN TRANSFER-REACTIONS OF O-IODOANILIDES

被引:83
作者
CURRAN, DP
YU, HS
LIU, HT
机构
[1] Department of Chemistry, University of Pittsburgh, Pittsburgh
关键词
D O I
10.1016/S0040-4020(01)90466-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best ''protecting/radical translocating'' (PRT) groups introduced to date. Beyond its good performance in radical translocation reactions, it is easy to introduce, serves as a reasonable protecting group both before and after the translocation, and (with appropriate modifications) is easy to remove.
引用
收藏
页码:7343 / 7366
页数:24
相关论文
共 72 条
[61]  
RIBAR DP, 1990, THESIS U PITTSBURGH
[62]  
Rylander P. N., 1979, CATALYTIC HYDROGENAT
[63]   NEW TANDEM RADICAL CYCLIZATIONS DIRECTED TOWARD THE SYNTHESIS OF CRINIPELLIN-A [J].
SCHWARTZ, CE ;
CURRAN, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9272-9284
[64]   GEMINAL PROTON NONEQUIVALENCES AND RELATED PHENOMENA IN SOME N-SUBSTITUTED AMIDES [J].
SIDDALL, TH ;
PROHASKA, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (06) :1172-&
[65]   SOME STUDIES OF SLOW ROTATIONS AROUND BONDS IN AMIDES [J].
SIDDALL, TH ;
GARNER, RH .
CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (20) :2387-&
[66]  
Snider B. B, 1991, CHEMTRACTS ORG CHEM, V4, P403
[67]   INTRAMOLECULAR ALPHA-AMIDOYL TO ARYL 1,5-HYDROGEN ATOM TRANSFER-REACTIONS - HETEROANNULATION AND ALPHA-NITROGEN FUNCTIONALIZATION BY RADICAL TRANSLOCATION [J].
SNIECKUS, V ;
CUEVAS, JC ;
SLOAN, CP ;
LIU, HT ;
CURRAN, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :896-898
[68]   NUCLEAR MAGNETIC RESONANCE STUDIES OF AMIDES [J].
STEWART, WE ;
SIDDALL, TH .
CHEMICAL REVIEWS, 1970, 70 (05) :517-&
[69]   PULSED-LASER INDUCED CHAIN ADDITION-REACTION OF PENTANAL TO DIETHYL MALEATE [J].
STRINGAT, R ;
FABRE, G ;
FELLOUS, R ;
PAQUET, P .
TETRAHEDRON LETTERS, 1992, 33 (30) :4303-4306
[70]   A NEW ROUTE TO THE PROSTAGLANDIN SKELETON VIA RADICAL ALKYLATION - SYNTHESIS OF 6-OXOPROSTAGLANDIN-E1 [J].
TORU, T ;
YAMADA, Y ;
UENO, T ;
MAEKAWA, E ;
UENO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4815-4817