Stereoselective synthesis of hydroxypyrrolidines and hydroxypiperidines by cyclization of gamma-oxygenated-alpha,beta-unsaturated sulfones

被引：32

作者：

Carretero, JC

Arrayas, RG

deGracia, IS

机构：

[1] Depto. de Quim. Orgánica, Facultad de Ciencias, Univ. Autónoma de Madrid

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 19期

关键词：

D O I：

10.1016/0040-4039(96)00551-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis and trans 2,3-disubstituted pyrrolidines and piperidines have been prepared stereoselectively by intramolecular conjugate addition of N-substituted gamma-oxygenated-alpha,beta-unsaturated phenyl sulfones. The best cis-selectivities were obtained from the alcohols and the best trans-selectivities from the OTIPS derivatives. (C) 1996 Published by Elsevier Science Ltd

引用

页码：3379 / 3382

页数：4

共 18 条

[1] AKIYAMA E, 1995, SYNLETT, P100
[2] EFFICIENT STEREOSELECTIVE ACCESS TO POLYHYDROXYLATED INDOLIZIDINE COMPOUNDS BASED ON GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFONES
CARRETERO, JC
ARRAYAS, RG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) : 6000 - 6001
[3] DAI WM, 1990, HETEROCYCLES, V30, P1231
[4] STEREOSELECTIVE APPROACH TO OPTICALLY PURE SYN 2-AMINO ALCOHOL DERIVATIVES
DEBLAS, J
CARRETERO, JC
DOMINGUEZ, E
[J]. TETRAHEDRON LETTERS, 1994, 35 (26) : 4603 - 4606
[5] A PRACTICAL ROUTE TO (E)-GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED PHENYL SULFONES
DOMINGUEZ, E
CARRETERO, JC
[J]. TETRAHEDRON, 1990, 46 (20) : 7197 - 7206
[6] MULTIPLY CONVERGENT SYNTHESES VIA CONJUGATE-ADDITION REACTIONS TO CYCLOALKENYL SULFONES
FUCHS, PL
BRAISH, TF
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 903 - 917
[7] PMR SPECTRA OF 1,2-SUBSTITUTED PROLINES
GALLINA, C
VIGLINO, P
PACI, M
[J]. OMR-ORGANIC MAGNETIC RESONANCE, 1972, 4 (01): : 31 - &
[8] DIASTEREOFACIAL SELECTIVITY IN INTRAMOLECULAR 1,4-CONJUGATE ADDITIONS - CONCLUSIVE EVIDENCE FOR THE IMPORTANCE OF GROUND-STATE CONFORMATIONS AND THE SIGMA(ASTERISK) ORBITAL EFFECT
GUNG, BW
FRANCIS, MB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) : 6177 - 6179
[9] THE DIASTEREOFACIAL SELECTIVITY IN THE INTRAMOLECULAR 1,4-CONJUGATE ADDITIONS GENERATING SUBSTITUTED TETRAHYDROTHIOPYRANS FOLLOWS THE CIEPLAK MODEL
GUNG, BW
FRANCIS, MB
[J]. TETRAHEDRON LETTERS, 1995, 36 (15) : 2579 - 2582
[10] CONJUGATE ADDITION OF INTERNAL NUCLEOPHILE TO CHIRAL VINYL SULFOXIDES WITH STEREOGENIC CENTER AT THE ALLYLIC CARBON - INTRAMOLECULAR DOUBLE ASYMMETRIC INDUCTION
HIRAMA, M
HIOKI, H
ITO, S
KABUTO, C
[J]. TETRAHEDRON LETTERS, 1988, 29 (25) : 3121 - 3124

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