Completely diastereoselective radical reactions using arenechromium tricarbonyl complexes

被引:41
作者
Merlic, CA [1 ]
Walsh, JC [1 ]
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(98)00267-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of chromium tricarbonyl complexed aryl aldehydes and ketones with samarium(Il) iodide and methyl acrylate results in formation of cyclic lactones as single diastereomers. Complete diastereoselectivity is demonstrated with aldehydes and ketones alpha or beta to the aromatic ring with radical coupling directed anti to the chromium tricarbonyl moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2083 / 2086
页数:4
相关论文
共 36 条
[1]  
[Anonymous], ADV METAL ORGANIC CH
[2]  
[Anonymous], 1995, Comprehensive Organometallic Chemistry II
[3]  
[Anonymous], ADV MET ORG CHEM, DOI DOI 10.1039/b205479p
[4]   Diastereoselective chelation-controlled radical cyclization of chiral oxazolidinone-derived 2-alkenamides and modeling of the transition state [J].
Badone, D ;
Bernassau, JM ;
Cardamone, R ;
Guzzi, U .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (05) :535-538
[5]   A totally radical approach to the control of stereochemistry: Coupling of prochiral radicals with chiral nitroxyl radicals [J].
Braslau, R ;
Burrill, LC ;
Mahal, LK ;
Wedeking, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :237-238
[6]   Catalytic reactions of samarium(II) iodide [J].
Corey, EJ ;
Zheng, GZ .
TETRAHEDRON LETTERS, 1997, 38 (12) :2045-2048
[7]   A COMPARISON OF THE RADICAL-STABILIZING ABILITY OF AROMATIC-GROUPS - GAMMA-VALUES FOR AROMATIC-GROUPS [J].
CREARY, X ;
MEHRSHEIKHMOHAMMADI, ME ;
MCDONALD, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2904-2910
[8]  
DAVIES SG, 1993, SYNLETT, P323
[9]   CHROMIUM DIRECTED REGIOCONTROL AND STEREOCONTROL - A NEW CHAPTER IN AROMATIC NATURAL PRODUCT SYNTHESIS [J].
DICKENS, PJ ;
GILDAY, JP ;
NEGRI, JT ;
WIDDOWSON, DA .
PURE AND APPLIED CHEMISTRY, 1990, 62 (04) :575-581
[10]   A facile synthesis of chiral gamma-butyrolactones in extremely high enantioselectivity mediated by samarium(II) iodide [J].
Fukuzawa, S ;
Seki, K ;
Tatsuzawa, M ;
Mutoh, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) :1482-1483