SYNTHESIS OF DIARYL DISELENIDES HAVING CHIRAL PYRROLIDINE RINGS WITH C-2 SYMMETRY - THEIR APPLICATION TO THE ASYMMETRIC METHOXYSELENENYLATION OF TRANS-BETA-METHYLSTYRENES

被引:101
作者
FUJITA, K [1 ]
IWAOKA, M [1 ]
TOMODA, S [1 ]
机构
[1] UNIV TOKYO, COLL ARTS & SCI, DEPT CHEM, MEGURO KU, TOKYO 153, JAPAN
关键词
D O I
10.1246/cl.1994.923
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Optically active diaryl diselenides carrying C-2 symmetrical chiral pyrrolidines are synthesized by the condensation between 2,2'-diselenobis(benzyl chloride) derivatives and chiral pyrrolidines and are applied to methoxyselenenylation of trans-olefins. The observed diastereomeric excess (d.e.) is up to 60%.
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页码:923 / 926
页数:4
相关论文
共 14 条
[1]   ASYMMETRIC OXIDATION OF SIMPLE SELENIDES TO SELENOXIDES IN HIGH ENANTIOPURITY - STEREOCHEMICAL ASPECTS OF THE ALLYL SELENOXIDE ALLYL SELENENATE REARRANGEMENT [J].
DAVIS, FA ;
REDDY, RT .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2599-2606
[2]   ASYMMETRIC SELENOMETHOXYLATION OF OLEFINS INVOLVING A CHIRAL C2 SYMMETRICAL ELECTROPHILIC ORGANOSELENIUM REAGENT [J].
DEZIEL, R ;
GOULET, S ;
GRENIER, L ;
BORDELEAU, J ;
BERNIER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3619-3621
[3]   ASYMMETRIC OXYSELENENYLATION OF OLEFINS USING OPTICALLY-ACTIVE SELENOBINAPHTHYLS AND D-MENTHOL AS A NUCLEOPHILE [J].
FUJITA, K ;
IWAOKA, M ;
TOMODA, S .
CHEMISTRY LETTERS, 1992, (07) :1123-1124
[4]   DIRECT OBSERVATION OF INTRAMOLECULAR INTERACTION BETWEEN A DIVALENT SELENIUM AND A TERTIARY AMINE BY MEANS OF SINGLE-CRYSTAL X-RAY-ANALYSIS AND NMR-SPECTROSCOPY [J].
IWAOKA, M ;
TOMODA, S .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 67 (1-4) :125-130
[5]   CATALYTIC CONVERSION OF ALKENES INTO ALLYLIC ETHERS AND ESTERS USING DISELENIDES HAVING INTERNAL TERTIARY-AMINES [J].
IWAOKA, M ;
TOMODA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1165-1167
[6]  
IWAOKA M, 1994, IN PRESS J AM CHEM S
[7]   ASYMMETRIC [2,3] SIGMATROPIC REARRANGEMENT VIA CHIRAL SELENOXIDE WITH SHARPLESS OXIDANTS [J].
KOMATSU, N ;
NISHIBAYASHI, Y ;
UEMURA, S .
TETRAHEDRON LETTERS, 1993, 34 (14) :2339-2342
[8]  
LUTHRA NP, 1986, CHEM ORGANIC SELENIU, V1
[9]   ASYMMETRIC-SYNTHESIS OF TRANS-(2R,5R)-BIS(BENZYLOXYMETHYL)PYRROLIDINE [J].
MARZI, M ;
MISITI, D .
TETRAHEDRON LETTERS, 1989, 30 (44) :6075-6076
[10]   ASYMMETRIC INDUCTION IN THE OXIDATION OF [2.2]PARACYCLOPHANE-SUBSTITUTED SELENIDES - APPLICATION OF CHIRALITY TRANSFER IN THE SELENOXIDE [2,3] SIGMATROPIC REARRANGEMENT [J].
REICH, HJ ;
YELM, KE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5672-5679