Stereospecific synthesis of optically active phenylpropylene oxides

被引:29
作者
Capriati, V
Florio, S
Luisi, R
Nuzzo, I
机构
[1] Univ Bari, Dipartimento Farmacochim, I-70126 Bari, Italy
[2] CNR, ICCOM, Sez Bari, Bari, Italy
关键词
D O I
10.1021/jo035858w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well as the trapping reaction with electrophiles. The reduction of the cis-alpha-benzoylpropylene oxide to give prevalently the anti-epoxy alcohol has been investigated as well.
引用
收藏
页码:3330 / 3335
页数:6
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[11]   THE REACTION OF DICHLOROCARBENE WITH BETA-ETHANOLAMINES STEREOSPECIFIC SYNTHESIS OF EPOXIDES [J].
CASTEDO, L ;
CASTRO, JL ;
RIGUERA, R .
TETRAHEDRON LETTERS, 1984, 25 (11) :1205-1208
[12]   Design of silica-supported dendritic chiral catalysts for the improvement of enantio selective addition of diethylzinc to benzaldehyde [J].
Chung, YM ;
Rhee, HK .
CATALYSIS LETTERS, 2002, 82 (3-4) :249-253
[13]   BASE-PROMOTED REACTIONS OF EPOXIDES .4. FORMATION OF SUBSTITUTED OLEFINS FROM REACTION OF EPOXIDES WITH ORGANOLITHIUM REAGENTS [J].
CRANDALL, JK ;
LIN, LHC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4527-&
[14]   BASE-PROMOTED REACTIONS OF EPOXIDES .3. CARBENOID DECOMPOSITION IN ACYCLIC DERIVATIVES [J].
CRANDALL, JK ;
LIN, LHC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4526-&
[15]   6-oxo-1,1,4,4-tetramethyl-1,4-diazepinium salts. A new class of catalysts for efficient epoxidation of olefins with oxone [J].
Denmark, SE ;
Wu, ZC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2810-2811
[16]  
Denmark SE, 1999, SYNLETT, P847
[17]   STEREOSPECIFIC SUBSTITUTED ALKENE SYNTHESIS BY ORGANO LITHIUM REDUCTIVE ALKYLATION OF EPOXIDES [J].
DORIS, E ;
DECHOUX, L ;
MIOSKOWSKI, C .
TETRAHEDRON LETTERS, 1994, 35 (43) :7943-7946
[18]   Oxiranyl and aziridinyl anions as reactive intermediates in synthetic organic chemistry - Preface [J].
Florio, S .
TETRAHEDRON, 2003, 59 (49) :9693-9693
[19]   THE STEREOCHEMISTRY OF THE 1-PHENYL-1,2-PROPANEDIOLS AND OF ALPHA-ISOEPHEDRINE [J].
FOLTZ, CM ;
WITKOP, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (01) :201-205
[20]  
GAWLEY RE, 1996, PRINCIPLE ASYMMETRIC