ASYMMETRIC MICHAEL ADDITION OF CHIRAL IMINES TO PHENYLVINYLSULFONE - PREPARATION OF KEY CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF ASPIDOSPERMA AND HUNTERIA ALKALOIDS

被引:25
作者
DANGELO, J [1 ]
REVIAL, G [1 ]
COSTA, PRR [1 ]
CASTRO, RN [1 ]
ANTUNES, OAC [1 ]
机构
[1] UNIV FED RIO DE JANEIRO,INST QUIM,BR-21941 RIO DE JANEIRO,BRAZIL
关键词
D O I
10.1016/S0957-4166(00)82358-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Addition of chiral imine 8 to phenylvinylsulfone 9 led, after hydrolytic work-up to adduct 11 (91 % stereoselectivity). This derivative has been converted into target cyclopentanones 14 and 16.
引用
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页码:199 / 202
页数:4
相关论文
共 16 条
[1]   A FACILE SYNTHESIS OF SPIROKETALS [J].
BRIMBLE, MA ;
OFFICER, DL ;
WILLIAMS, GM .
TETRAHEDRON LETTERS, 1988, 29 (29) :3609-3612
[2]  
CORDELL GA, 1979, ALKALOIDS, V17
[3]   THE ASYMMETRIC MICHAEL ADDITION PROCESS INVOLVING CHIRAL IMINES - STEREOCHEMICAL DATA IN SUPPORT OF A CYCLIC-LIKE TRANSITION-STATE [J].
DANGELO, J ;
GUINGANT, A ;
RICHE, C ;
CHIARONI, A .
TETRAHEDRON LETTERS, 1988, 29 (22) :2667-2670
[4]   A NEW STRATEGY FOR THE ENANTIOSELECTIVE SYNTHESIS OF ASPIDOSPERMA ALKALOIDS .1. CONSTRUCTION OF THE [ABC]-TYPE TRICYCLIC INTERMEDIATES [J].
DANGELO, J ;
DESMAELE, D .
TETRAHEDRON LETTERS, 1990, 31 (06) :879-882
[5]   THE ASYMMETRIC MICHAEL PROCESS INVOLVING CHIRAL IMINES - THE DIASTEREOFACIAL DIFFERENTIATION ASPECT [J].
DANGELO, J ;
REVIAL, G ;
GUINGANT, A ;
RICHE, C ;
CHIARONI, A .
TETRAHEDRON LETTERS, 1989, 30 (20) :2645-2648
[6]   A NEW STRATEGY FOR THE ENANTIOSELECTIVE SYNTHESIS OF ASPIDOSPERMA ALKALOIDS .2. ACHIEVEMENT OF THE PENTACYCLIC SYSTEM [J].
DESMAELE, D ;
DANGELO, J .
TETRAHEDRON LETTERS, 1990, 31 (06) :883-886
[7]   ASYMMETRIC-SYNTHESIS OF FURANONES [J].
DESMAELE, D ;
DANGELO, J ;
BOIS, C .
TETRAHEDRON-ASYMMETRY, 1990, 1 (11) :759-762
[8]  
DOPKE W, 1981, ALKALOIDS, V20
[9]   INTRAMOLECULAR MICHAEL ADDITION OF CHIRAL IMINES TO ENOATES - A NEW ASYMMETRIC CARBOCYCLIZATION REACTION [J].
DUMAS, F ;
DANGELO, J .
TETRAHEDRON-ASYMMETRY, 1990, 1 (03) :167-170
[10]  
IHARA M, 1990, HETEROCYCLES, V31, P1017