Sequenced reactions with samarium(II)Iodide. Tandem nucleophilic acyl substitution/ketyl-olefin coupling reactions

被引:72
作者
Molander, GA
Harris, CR
机构
[1] Department of Chemistry, University of Colorado, Boulder
关键词
D O I
10.1021/ja952619k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Samarium(II) iodide has been employed to promote a tandem intramolecular nucleophilic acyl substitution/intramolecular ketyl-olefin coupling cyclization sequence, generating bicyclic, tricyclic, and spirocyclic ring systems in excellent yield and with high diastereoselectivity. This versatile reaction sequence allows entry to several different naturally occurring tricyclic systems containing the angular and linear triquinane framework.
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页码:4059 / 4071
页数:13
相关论文
共 56 条
[1]   THE EFFECT OF REACTOR SURFACES ON SINGLE-ELECTRON TRANSFER-REACTIONS - THE REACTION OF 1-IODO-2,2-DIMETHYLHEXANE WITH LITHIUM ALUMINUM DEUTERIDE [J].
ASHBY, EC ;
WELDER, CO .
TETRAHEDRON LETTERS, 1995, 36 (40) :7171-7174
[2]   SAMARIUM(II) IODIDE PROMOTED RADICAL RING-OPENING REACTIONS OF CYCLOPROPYL KETONES [J].
BATEY, RA ;
MOTHERWELL, WB .
TETRAHEDRON LETTERS, 1991, 32 (45) :6649-6652
[3]  
BROWN HC, 1975, ORGANIC SYNTHESES VI
[4]   FUNCTIONALIZED CARBOCYCLES BY TANDEM DEALKOXYCARBONYLATION MICHAEL ADDITION-REACTIONS [J].
BUNCE, RA ;
DOWDY, ED ;
JONES, PB ;
HOLT, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7143-7148
[5]   NONTOXIC LIGANDS IN SAMARIUM DIIODIDE-MEDIATED CYCLIZATIONS [J].
CABRI, W ;
CANDIANI, I ;
COLOMBO, M ;
FRANZOI, L ;
BEDESCHI, A .
TETRAHEDRON LETTERS, 1995, 36 (06) :949-952
[6]   STUDIES WITH TRIALKYLSILYLTRIFLATES - NEW SYNTHESES AND APPLICATIONS [J].
COREY, EJ ;
CHO, H ;
RUCKER, C ;
HUA, DH .
TETRAHEDRON LETTERS, 1981, 22 (36) :3455-3458
[7]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[8]  
CURRAN DP, 1990, SYNLETT, P773
[9]   NEW SEQUENTIAL CARBON-CARBON BOND FORMING REACTIONS - A SAMARIUM(II) IODIDE MEDIATED VINYLOGOUS BARBIER REACTION FOLLOWED BY AN ALDOL REACTION [J].
CURRAN, DP ;
WOLIN, RL .
SYNLETT, 1991, (05) :317-318
[10]   SILICON-DIRECTED NAZAROV CYCLIZATIONS .4. FURTHER-STUDIES IN STEREOCHEMICAL CONTROL [J].
DENMARK, SE ;
HABERMAS, KL ;
HITE, GA ;
JONES, TK .
TETRAHEDRON, 1986, 42 (11) :2821-2829