Radicals from epoxides.: Intramolecular addition to aldehyde and ketone carbonyls

被引:90
作者
Fernández-Mateos, A [1 ]
de la Nava, EM [1 ]
Coca, GP [1 ]
Silvo, AR [1 ]
González, RR [1 ]
机构
[1] Univ Salamanca, Fac Quim, Dept Quim Organ, E-37008 Salamanca, Spain
关键词
D O I
10.1021/ol990699h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Titanocene chloride reacts with epoxides by C-O homolysis with clean regioselectivity. The resultant radicals undergo intramolecular addition to aldehyde and ketone carbonyls to afford cycloalkanols in good yields. The behavior of epoxy alcohols with titanocene chloride to afford saturated diols and epoxy esters that give unsaturated hydroxy esters deserve special mention.
引用
收藏
页码:607 / 609
页数:3
相关论文
共 16 条
[1]   KINETICS OF THE REVERSIBLE BETA-SCISSION OF THE CYCLOPENTYLOXY RADICAL [J].
BECKWITH, ALJ ;
HAY, BP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :230-234
[2]   The scope and limitations of intramolecular radical cyclizations of acylsilanes with alkyl, aryl, and vinyl radicals [J].
Chang, SY ;
Jiaang, WT ;
Cherng, CD ;
Tang, KH ;
Huang, CH ;
Tsai, YM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9089-9098
[3]   On the mechanism of the intramolecular samarium Barbier reaction. Probes for formation of radical and organosamarium intermediates [J].
Curran, DP ;
Gu, X ;
Zhang, W ;
Dowd, P .
TETRAHEDRON, 1997, 53 (27) :9023-9042
[4]   Radical cyclizations of acylgermanes. New reagent equivalents of the carbonyl radical acceptor synthon [J].
Curran, DP ;
Diederichsen, U ;
Palovich, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4797-4804
[5]  
CURRAN DP, 1991, COMPREHENSIVE ORGANI, V4, P815
[6]   FREE RADICAL-MEDIATED RING EXPANSION AND RELATED ANNULATIONS [J].
DOWD, P ;
ZHANG, W .
CHEMICAL REVIEWS, 1993, 93 (06) :2091-2115
[7]  
Gansäuer A, 1998, ANGEW CHEM INT EDIT, V37, P101, DOI 10.1002/(SICI)1521-3773(19980202)37:1/2<101::AID-ANIE101>3.0.CO
[8]  
2-W
[9]  
Gansauer A, 1998, SYNLETT, P801
[10]   PREPARATION OF BETA-CYCLOCITRAL [J].
GEDYE, RN ;
ARORA, PC ;
DECK, K .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (10) :1764-&