A NEW ROUTE TO ENANTIOMERICALLY PURE 2,5-DISUBSTITUTED PYRROLIDINES - TOTAL SYNTHESIS OF (+)-PYRROLIDINE 197B

被引：10

作者：

BLOCH, R

BRILLETFERNANDEZ, C

MANDVILLE, G

机构：

[1] Laboratoire des Carbocycles, Associé au CNRS, Institut de Chimie Moléculaire d'Orsay, 91405 Orsay Cedex

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 04期

关键词：

D O I：

10.1016/0957-4166(94)80037-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An enantioselective synthesis of (+)-pyrrolidine 197B, starting from the readily available lactol 1 is described. The key steps involve two chelation controlled additions of Grignard reagents to the carbonyl groups of lactols 1 and 5 and a highly stereoselective trans-pyrrolidine formation from the dimesylate 9.

引用

收藏

页码：745 / 750

页数：6

相关论文

共 20 条

[1] ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING [J].

ARSENIYADIS, S ;

HUANG, PQ ;

PIVETEAU, D ;

HUSSON, HP .

TETRAHEDRON, 1988, 44 (09) :2457-2470

[2]

BACKVALL JE, 1990, J ORG CHEM, V55, P826, DOI 10.1021/jo00290a010

[3] STEREOSELECTIVE REACTIONS INDUCED BY A THERMOLABILE GROUP - CHELATION AND NON CHELATION CONTROLLED ADDITIONS OF ORGANOMETALLICS TO A DIELS-ALDER ADDUCT OF FURAN [J].

BLOCH, R ;

GILBERT, L .

TETRAHEDRON LETTERS, 1987, 28 (04) :423-426

[4] STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES [J].

BLOCH, R ;

GUIBEJAMPEL, E ;

GIRARD, C .

TETRAHEDRON LETTERS, 1985, 26 (34) :4087-4090

[5]

BLOCH R, 1991, SYNLETT, P829

[6]

BLOCH R, 1992, ASYMMETRY, V3, P333

[7] ALKALOIDS FROM DENDROBATID FROGS - STRUCTURES OF 2 OMEGA-HYDROXY CONGENERS OF 3-BUTYL-5-PROPYLINDOLIZIDINE AND OCCURRENCE OF 2,5-DISUBSTITUTED PYRROLIDINES AND A 2,6-DISUBSTITUTED PIPERIDINE [J].

DALY, JW ;

SPANDE, TF ;

WHITTAKER, N ;

HIGHET, RJ ;

FEIGL, D ;

NISHIMORI, N ;

TOKUYAMA, T ;

MYERS, CW .

JOURNAL OF NATURAL PRODUCTS, 1986, 49 (02) :265-280

[8]

DMAS F, 1992, TETRAHEDRON LETT, V23, P2005

[9]

Griffith W. P., 1990, ALDRICHIM ACTA, V23, P13

[10] MAGNETIC NON-EQUIVALENCE OF METHYLENE PROTONS IN DISSYMMETRIC BENZYLAMINES - A SIMPLE METHOD OF ASSIGNMENT OF CONFIGURATION TO IDENTICALLYALPHA,ALPHA'-DISUBSTITUTED HETEROCYCLIC BASES [J].

HILL, RK ;

CHAN, TH .

TETRAHEDRON, 1965, 21 (08) :2015-&