SOME DIASTEREOSELECTIVE RADICAL REACTIONS OF SUBSTITUTED 1,3-DIOXOLAN-4-ONES

被引:24
作者
BECKWITH, ALJ
CHAI, CLL
机构
[1] Research School of Chemistry, Australian National University, Canberra, ACT 2001, Australia
关键词
D O I
10.1016/S0040-4020(01)88012-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The radical 3, generated (i) from reactions of 5-substituted 2-tert-butyl-1,3-dioxolan-4-ones with N-bromosuccinimide, (ii) from related bromo compounds by reaction with tributylstannane or with allyltributyltin, and (iii) by radical addition to 5-methylene-1,3-dioxolan-4-one, undergoes carbon-bromine, carbon-hydrogen, and carbon-carbon bond formation trans to the tert-butyl group with moderate to high diastereoselectivity
引用
收藏
页码:7871 / 7882
页数:12
相关论文
共 25 条
[1]   FREE-RADICAL REACTIONS OF ORGANOMERCURIALS [J].
BARLUENGA, J ;
YUS, M .
CHEMICAL REVIEWS, 1988, 88 (03) :487-509
[2]   THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
TETRAHEDRON, 1985, 41 (19) :3901-3924
[3]   FORMATION OF SOME BICYCLIC AND TRICYCLIC SYSTEMS BY RADICAL RING-CLOSURE [J].
BECKWITH, ALJ ;
ROBERTS, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5893-5901
[4]   2-(TERT-BUTYL)-CIS-5-(PARA-CHLOROPHENYLTHIO)-TRANS-5-METHYL-1,3-DIOXOLAN-4-ONE [J].
BECKWITH, ALJ ;
CHAI, CLL ;
WILLIS, AC .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 :1362-1364
[5]   AN EPR STUDY OF FREE-RADICALS DERIVED FROM 1,3-DIOXOLAN-4-ONE AND RELATED-COMPOUNDS [J].
BECKWITH, ALJ ;
BRUMBY, S ;
CHAI, CLL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (12) :2117-2121
[6]  
Chai C.-L., UNPUB
[7]  
CHAI CLL, 1990, J CHEM SOC CHEM COMM, P1087
[8]   A NEW HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF 2,5-DISUBSTITUTED-1,3-DIOXOLAN-4-ONES FROM ALPHA-HYDROXYACIDS [J].
CHAPEL, N ;
GREINER, A ;
ORTHOLAND, JY .
TETRAHEDRON LETTERS, 1991, 32 (11) :1441-1442
[9]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[10]   POLAR SUBSTITUENT EFFECTS IN ADDITIONS OF ALKYL RADICALS TO ALKENES [J].
GIESE, B ;
MEIXNER, J .
CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (06) :2138-2145