ENANTIOSELECTIVE RADICAL CYCLIZATION FOR THE SYNTHESIS OF CYCLIC COMPOUNDS

被引:25
作者
Yoshioka, Eito [1 ]
Kohtani, Shigeru [1 ]
Miyabe, Hideto [1 ]
机构
[1] Hyogo Univ Hlth Sci, Sch Pharm, Chuo Ku, Kobe, Hyogo 6508530, Japan
关键词
Radical; Cyclization; Enantioselective Reaction; Lewis Acid; Organocatalyst; CHIRAL LEWIS-ACID; CARBON-CARBON BOND; ATOM TRANSFER-REACTIONS; ADDITION-CYCLIZATION; FORMING REACTIONS; TIN HYDRIDE; CONSTRUCTION; ALLYLATION;
D O I
10.3987/REV-08-SR(D)8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review highlights the enantioselective radical cyclization reactions catalyzed by chiral Lewis acid as well as organocatalyst. The results of the radical cyclization controlled by chiral Al, Ti, Mg, Yb and Zn reagents, the oxidative cyclization using chiral amine, the chiral complexing agent-catalyzed reductive cyclization, transfer of chirality in radical cyclization, and so on are summarized.
引用
收藏
页码:229 / 242
页数:14
相关论文
共 45 条
[1]   Hydrogen bond mediated enantioselectivity of radical reactions [J].
Aechtner, T ;
Dressel, M ;
Bach, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (43) :5849-5851
[2]   Stereoselective radical reactions [J].
Bar, G ;
Parsons, AF .
CHEMICAL SOCIETY REVIEWS, 2003, 32 (05) :251-263
[3]   Catalytic enantioselective reactions driven by photoinduced electron transfer [J].
Bauer, A ;
Westkämper, F ;
Grimme, S ;
Bach, T .
NATURE, 2005, 436 (7054) :1139-1140
[4]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].
BECKWITH, ALJ .
TETRAHEDRON, 1981, 37 (18) :3073-3100
[5]   Enantioselective organocatalysis using SOMO activation [J].
Beeson, Teresa D. ;
Mastracchio, Anthony ;
Hong, Jun-Bae ;
Ashton, Kate ;
MacMillan, David W. C. .
SCIENCE, 2007, 316 (5824) :582-585
[6]   Enantioselective hydrogen transfer from a chiral tin hydride to a prochiral carbon-centered radical [J].
Blumenstein, M ;
Schwarzkopf, K ;
Metzger, JO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :235-236
[7]   Carbohydrate-derived thiols as protic polarity-reversal catalysts for enantioselective radical-chain reactions [J].
Cai, YD ;
Roberts, BP ;
Tocher, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (11) :1376-1386
[8]  
Corminboeuf O, 2003, CHEM-EUR J, V9, P29
[9]   N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions [J].
Corminboeuf, O ;
Renaud, P .
ORGANIC LETTERS, 2002, 4 (10) :1735-1738
[10]   Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide [J].
Corminboeuf, O ;
Renaud, P .
ORGANIC LETTERS, 2002, 4 (10) :1731-1733