Asymmetric synthesis of functionalized piperidine derivatives:: synthesis of (S)-anatabine

被引：39

作者：

Balasubramanian, T ^{[1
]}

Hassner, A ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(98)00225-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A short and efficient chiral synthesis of 6-aryl-5-phenylsulfonyl-1,2,5,6-tetrahydropyridines was achieved in moderate yield and with good selectivity. The absolute configurations were assigned by extending the methodology to (S)-anatabine and as well with NMR experiments. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2201 / 2205

页数：5

共 40 条

[1] Cyclization of a chiral oxazolidine as a key-step for the synthesis of functionalized piperidines
Agami, C
Couty, F
Mathieu, H
[J]. TETRAHEDRON LETTERS, 1996, 37 (23) : 4001 - 4002
[2] Synthesis of enantiopure piperidines. Total synthesis of (2R,6S)-2-methyl-6-propylpiperidine [(-)-dihydropinidine]
Amat, M
Llor, H
Hidalgo, J
Hernandez, A
Bosch, J
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (04) : 977 - 980
[3] Stereochemistry .87. Synthesis of chiral non-racemic 2-arylpyrrolines by a [3+2] cycloaddition route
Balasubramanian, T
Hassner, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (32) : 5755 - 5758
[4] COLONGE J, 1955, B SOC CHIM FR, P953
[5] Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones
Comins, DL
Joseph, SP
Hong, H
Alawar, RS
Foti, CJ
Zhang, YM
Chen, XH
LaMunyon, DH
GuerraWeltzien, M
[J]. PURE AND APPLIED CHEMISTRY, 1997, 69 (03) : 477 - 481
[6] Cossy J, 1997, SYNLETT, P905
[7] Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides)
Davis, FA
Reddy, RE
Szewczyk, JM
Reddy, GV
Portonovo, PS
Zhang, HM
Fanelli, D
Reddy, RT
Zhou, P
Carroll, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) : 2555 - 2563
[8] ASYMMETRIC-SYNTHESIS OF SULFINIMINES - CHIRAL AMMONIA IMINE SYNTHONS
DAVIS, FA
REDDY, RE
SZEWCZYK, JM
PORTONOVO, PS
[J]. TETRAHEDRON LETTERS, 1993, 34 (39) : 6229 - 6232
[9] Regioselective alkylation of N-(diphenylmethylidine)3-(aminomethyl)pyrudube: A simple route to minor tobacco alkaloids and related compounds
Deo, NM
Crooks, PA
[J]. TETRAHEDRON LETTERS, 1996, 37 (08) : 1137 - 1140
[10] MINOR ALKALOIDS OF TOBACCO RELEASE [H-3] DOPAMINE FROM SUPERFUSED RAT STRIATAL SLICES
DWOSKIN, LP
TENG, LH
BUXTON, ST
RAVARD, A
DEO, N
CROOKS, PA
[J]. EUROPEAN JOURNAL OF PHARMACOLOGY, 1995, 276 (1-2) : 195 - 199

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