2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: A privileged, bivalent scaffold for the display of nucleophilic components

被引:39
作者
Converso, A
Burow, K
Marzinzik, A
Sharpless, KB
Finn, MG
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Ins Chem Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/jo015632y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound, the condensation product of sulfur dichloride and 1,5-cyclooctadiene, is a reliable acceptor of a wide variety of heteroatom nucleophiles, sometimes in reversible fashion. Optical resolution of the core structure has been achieved and preserved in succeeding transformations. The high reactivity and reliable stereochemical control afforded by this system illustrates the power of neighboring-group participation by the sulfur center.
引用
收藏
页码:4386 / 4392
页数:7
相关论文
共 48 条
[1]   SULFENYL CHLORIDE CHEMISTRY - SULFUR TRANSFER TO DOUBLE-BONDS [J].
ABUYOUSEF, IA ;
HYNES, RC ;
HARPP, DN .
TETRAHEDRON LETTERS, 1993, 34 (27) :4289-4292
[2]  
[Anonymous], 1966, CHEM ORGANIC SULFUR, V2, P73
[3]  
Bishop R, 1992, ORG SYNTH, V70, P120
[4]   PREPARATION OF EPISULFIDES FROM ALKENES VIA SUCCINIMIDE-N-SULFENYL CHLORIDE OR PHTHALIMIDE-N-SULFENYL CHLORIDE ADDUCTS [J].
BOMBALA, MU ;
LEY, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12) :3013-3016
[5]  
Capozzi G., 1990, CHEM SULPHENIC ACIDS
[6]   Anchimeric assistance by the anomeric phenylthio group in the nucleophilic substitution of a 6-O-trifluoromethanesulfonyl-β-D-galactopyranoside [J].
Compain-Batissou, M ;
Mesrari, L ;
Anker, D ;
Doutheau, A .
CARBOHYDRATE RESEARCH, 1999, 316 (1-4) :201-205
[7]   CIS,CIS-1,5-CYCLOOCTADIENE DIEPOXIDE [J].
COPE, AC ;
FISHER, BS ;
FUNKE, W ;
MCINTOSH, JM ;
MCKERVEY, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (07) :2231-&
[8]   NEW SYNTHETIC APPROACHES TO SYMMETRICAL SULFUR-BRIDGED CARBOCYCLES [J].
COREY, EJ ;
BLOCK, E .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (06) :1663-&
[9]   X-ray structures and anionotropic rearrangements of di-tert-butyl-substituted thiiranium and thiirenium ions.: A structure-reactivity relationship [J].
Destro, R ;
Lucchini, V ;
Modena, G ;
Pasquato, L .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3367-3370
[10]  
DITTMER DC, 1981, CHEM SULPHONIUM GROU, P387