NEW CONVENIENT, ENANTIOSPECIFIC SYNTHESIS OF (S,S)-2,2'-BIPYRROLIDINE AND (R,R)-2,2'-BIPYRROLIDINE DERIVATIVES

被引：25

作者：

KOTSUKI, H

KUZUME, H

GOHDA, T

FUKUHARA, M

OCHI, M

OISHI, T

HIRAMA, M

SHIRO, M

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

[2] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 09期

关键词：

D O I：

10.1016/0957-4166(95)00297-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An enantiomeric pair of (S,S)- and (R,R)-bipyrrolidine derivatives has been prepared from D-and L-tartaric acids or D-mannitol as optically active starting materials. Taking advantage of the C-2-symmetric nature of these chiral sources, the synthetic sequence has been established by using efficient side chain elongation, stereospecific conversion of a vicinal diol into a diazido group via S(N)2 inversion, and pyrrolidine ring formation via intramolecular substitution as the key steps.

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页码：2227 / 2236

页数：10

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共 98 条

[41] ASYMMETRIC DIHYDROXYLATION OF OLEFINS WITH A SIMPLE CHIRAL LIGAND [J].

HANESSIAN, S ;

MEFFRE, P ;

GIRARD, M ;

BEAUDOIN, S ;

SANCEAU, JY ;

BENNANI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :1991-1993

[42] VERSATILE SYNTHESIS OF ALICYCLIC AND ACYCLIC COMPOUNDS WITH ALTERNATE AND REMOTE C-METHYL SUBSTITUTION PATTERNS VIA ASYMMETRIC SEQUENTIAL OLEFINATION AND ENE REACTIONS [J].

HANESSIAN, S ;

BEAUDOIN, S .

TETRAHEDRON LETTERS, 1992, 33 (50) :7659-7662

[43] OPTICAL RESOLUTION OF TRANS-BICYCLO[2.2.1]HEPTANE-2,3-DIAMINE - CHIRAL RECOGNITION IN THE CRYSTAL OF ITS COMPLEX WITH (2R,3R)-O,O'-DIBENZOYLTARTARIC ACID [J].

HATANO, K ;

TAKEDA, T ;

SAITO, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (03) :579-584

[44] ASYMMETRIC DIHYDROXYLATION OF ALKENES WITH OSMIUM-TETROXIDE - CHIRAL N,N'-DIALKYL-2,2'-BIPYRROLIDINE COMPLEX [J].

HIRAMA, M ;

OISHI, T ;

ITO, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (10) :665-666

[45] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL ZINC(II) COMPLEXES [J].

JANSEN, JFGA ;

FERINGA, BL .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :4168-4175

[46]

JOHNSON CK, ORNL5138 ORTEP 2 REP

[47] C-2-SYMMETRIC 1,2-DIAMINE/COPPER(II) TRIFLUOROMETHANESULFONATE COMPLEXES AS CHIRAL CATALYSTS - ASYMMETRIC CYCLOPROPANATIONS OF STYRENE WITH DIAZO ESTERS [J].

KANEMASA, S ;

HAMURA, S ;

HARADA, E ;

YAMAMOTO, H .

TETRAHEDRON LETTERS, 1994, 35 (43) :7985-7988

[48] DIRECT OPTICAL RESOLUTION OF VICINAL DIOLS AND AN ALPHA-HYDROXY OXIME WITH A VICINAL DIAMINE [J].

KAWASHIMA, M ;

HIRAYAMA, A .

CHEMISTRY LETTERS, 1991, (05) :763-766

[49] ANTI-SELECTIVE ASYMMETRIC ALDOL REACTIONS - ENANTIOSELECTIVE SYNTHESIS OF ANTI-ALPHA,BETA-DIHYDROXY PHENYL ESTER DERIVATIVES [J].

KOBAYASHI, S ;

KAWASUJI, T .

TETRAHEDRON LETTERS, 1994, 35 (20) :3329-3332

[50] CHIRAL LEWIS-ACID-CONTROLLED SYNTHESIS OF BOTH DIASTEREOMERS - ENANTIOSELECTIVE SYNTHESIS OF BOTH SYN-2,3-DIHYDROXY AND ANTI-2,3-DIHYDROXY ESTER DERIVATIVES FROM THE SAME STARTING MATERIALS VIA ASYMMETRIC ALDOL REACTIONS BY CHOICE OF CHIRAL LIGANDS [J].

KOBAYASHI, S ;

HAYASHI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1098-1099

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