(SS)-2-(p-tolylsulfinyl)norborneno-p-benzoquinones: A new type of facially perturbed enantiopure quinones

被引:26
作者
Carreno, MC [1 ]
Ruano, JLG [1 ]
Urbano, A [1 ]
LopezSolera, MI [1 ]
机构
[1] UNIV AUTONOMA MADRID,DEPT QUIM ORGAN CVIII,E-28049 MADRID,SPAIN
关键词
D O I
10.1021/jo9618942
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses and asymmetric Diels-Alder reactions of (SS)-2-(p-tolylsulfinyl)norboreno-p-benzoquinones 10 and 11 with cyclopentadiene are reported. The cycloadditions allowed the highly stereoselective obtention of the four possible endo adducts 12-15, optically pure synthetic equivalents of norborneno-p-benzoquinone-cyclopentadiene bisadducts. The detailed study of the H-1-NMR spectra of the adducts pointed out the anisotropic effects exerted by the sulfinyl moiety on the spectroscopic behavior of these rigid systems. In all cases, the pi-facial selectivities were fully controlled by the sulfinyl group being possible to reverse the diastereoselection in thermal conditions and in the presence of ZnBr2. The stereoselective synthesis of the cage compound 5, precursor of garudane, was achieved from cycloadduct endo-syn-13.
引用
收藏
页码:976 / 981
页数:6
相关论文
共 48 条
[41]   HETEROATOMIC INFLUENCES ON THE PI-FACIAL SELECTIVITY OF DIELS-ALDER CYCLOADDITIONS TO DISPIRO[4.0.4.4]TETRADECA-11,13-DIENES [J].
PAQUETTE, LA ;
BRANAN, BM ;
ROGERS, RD ;
BOND, AH ;
LANGE, H ;
GLEITER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5992-6001
[42]   THE NON-PLANARITY OF THE BICYCLO[2.2.1]HEPT-2-ENE DOUBLE-BOND - CRYSTAL-STRUCTURES OF BICYCLO[2.2.2]OCT-2-ENE, BICYCLO[2.2.1]HEPT-2-ENE, AND BICYCLO[2.1.1]HEX-2-ENE SYSTEMS [J].
PINKERTON, AA ;
SCHWARZENBACH, D ;
BIRBAUM, JL ;
CARRUPT, PA ;
SCHWAGER, L ;
VOGEL, P .
HELVETICA CHIMICA ACTA, 1984, 67 (04) :1136-1153
[43]   ENANTIOSELECTIVE SYNTHESIS OF 2-ALKYL-5-METHYLENE-1,3-DIOXOLAN-4-ONES AND EXO-SELECTIVE DIELS-ALDER REACTIONS WITH CYCLOPENTADIENE [J].
ROUSH, WR ;
BROWN, BB .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3380-3387
[44]   THEORETICAL SECONDARY KINETIC ISOTOPE EFFECTS AND THE INTERPRETATION OF TRANSITION-STATE GEOMETRIES .2. THE DIELS-ALDER REACTION TRANSITION-STATE GEOMETRY [J].
STORER, JW ;
RAIMONDI, L ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (21) :9675-9683
[45]  
TROST BM, 1991, COMPREHENSIVE ORGANI, V5, pCH4
[46]   PI-FACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF [4.3.2]PROPELLA-2,4,8,10-TETRAEN-7-ONE AND ITS DERIVATIVES - SYNTHESIS OF 2,5-ETHENO[4.3.2]PROPELLA-3,8,10-TRIEN-7-ONES [J].
TSUJI, T ;
OHKITA, M ;
NISHIDA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :997-1003
[47]  
WATSON WH, 1983, STEREOCHEMISTRY REAC
[48]  
[No title captured]