SYNTHESIS OF A CHIRAL BINAPHTHYLDISULFIDE - A POTENTIALLY USEFUL REAGENT FOR CATALYTIC ASYMMETRIC-SYNTHESIS

被引:15
作者
FELDMAN, KS
RUCKLE, RE
ENSEL, SM
WEINREB, PH
机构
[1] Chemistry Department, The Pennsylvania State University University Park
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)60846-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diels Alder cycloaddition/oxygen-atom-extrusion provides the means to unite two naphthylene fragments and affords a highly functionalized, racemic binaphthyl iodide. Resolution of a derived thiol then furnishes, after appropriate manipulation, enantiomerically pure binaphthyldisulfide precatalysts.
引用
收藏
页码:7101 / 7102
页数:2
相关论文
共 12 条
[1]   REARRANGEMENT + CLEAVAGE OF 2-ARYLIODONIOBENZOATES - TRAPPING AGENTS FOR BENZYNE [J].
BERINGER, FM ;
HUANG, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (02) :445-&
[2]   INTERACTIONS AND CHEMISTRY OF 1,8-BIS(PHENYLETHYNYL)-NAPHTHALENE AND 1,8-BIS(1-ALKYNYL)NAPHTHALENES [J].
BOSSENBROEK, B ;
SANDERS, DC ;
CURRY, HM ;
SHECHTER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (02) :371-+
[3]   CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .13. AN ATTEMPTED SYNTHESIS OF 1,2-DIPHENYLBENZOCYCLOBUTENE [J].
CAVA, MP ;
MITCHELL, MJ ;
DEANA, AA .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (09) :1481-1484
[4]   NONCLASSICAL CONDENSED THIOPHENES .6. ISOTHIANAPHTHENE 2,2-DIOXIDES [J].
CAVA, MP ;
MCGRADY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (01) :72-77
[5]   HOST-GUEST COMPLEXATION .9. MACROCYCLIC POLYETHERS AND SULFIDES SHAPED BY ONE RIGID DINAPHTHYL UNIT AND ATTACHED ARMS - SYNTHESIS AND SURVEY OF COMPLEXING ABILITIES [J].
CRAM, DJ ;
HELGESON, RC ;
KOGA, K ;
KYBA, EP ;
MADAN, K ;
SOUSA, LR ;
SIEGEL, MG ;
MOREAU, P ;
GOKEL, GW ;
TIMKO, JM ;
SOGAH, GDY .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2758-2772
[6]   ASYMMETRIC REACTIONS OF THIOACETALS AND THEIR S-OXIDES DERIVED FROM 1,1'-BINAPHTHALENE-2,2'-DITHIOL [J].
DELOGU, G ;
DELUCCHI, O ;
MAGLIOLI, P ;
VALLE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4467-4473
[7]   VINYLCYCLOPENTANE SYNTHESIS VIA PHENYLTHIO RADICAL CATALYZED ALKENYLATION OF VINYLCYCLOPROPANES - PREPARATIVE AND MECHANISTIC STUDIES [J].
FELDMAN, KS ;
ROMANELLI, AL ;
RUCKLE, RE ;
JEAN, G .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :100-110
[8]   OXYGENATION OF SUBSTITUTED VINYLCYCLOPROPANES - PREPARATIVE AND MECHANISTIC STUDIES [J].
FELDMAN, KS ;
SIMPSON, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4878-4886
[9]   SYNTHESIS OF VINYLCYCLOPENTANES FROM VINYLCYCLOPROPANES AND ALKENES PROMOTED BY BENZENETHIYL RADICAL [J].
MIURA, K ;
FUGAMI, K ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1988, 29 (40) :5135-5138
[10]   [3+2] METHYLENECYCLOPENTANE ANNULATIONS OF UNACTIVATED AND ELECTRON-RICH OLEFINS WITH 2-(PHENYLSULFONYL)-1-METHYLENECYCLOPROPANES [J].
SINGLETON, DA ;
CHURCH, KM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4780-4782