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

[31] Asymmetric synthesis of cis-(-)-(2R4S)-4-(phosphonomethyl)-2-piperidinecarboxylic acid, a potent NMDA receptor antagonist
Skiles, JW
Giannousis, PP
Fales, KR
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (08) : 963 - 966
[32] CONVERSION OF ALLYLIC ALCOHOLS TO CHLORIDES WITHOUT REARRANGEMENT
SNYDER, EI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (09) : 1466 - &
[33] l-anatabine, a new tobacco alkaloid (XI. Announcement on the tobacco bases).
Spath, E
Kesztler, F
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1937, 70 : 239 - 243
[34] The appearance of delta,lambda-nor-nicotine, delta,lambda-anatabine and lambda-anabasine in tobacco (XII. Announcement on tobacco alkaloids).
Spath, E
Kesztler, F
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1937, 70 : 704 - 709
[35] A general entry to 2-(2-hydroxyalkyl)piperidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement
Takahata, H
Kubota, M
Momose, T
[J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3451 - 3454
[36] RECENT ADVANCES IN DIANION CHEMISTRY
THOMPSON, CM
GREEN, DLC
[J]. TETRAHEDRON, 1991, 47 (25) : 4223 - 4285
[37] TROSTBM, 1976, TETRAHEDRON LETT, P3477
[38] ASYMMETRIC ELECTROPHILIC ALPHA-AMIDOALKYLATION .10. A NEW CAMPHORIMIDE DERIVED CHIRAL AUXILIARY FOR THE ASYMMETRIC-SYNTHESIS WITH N-ACYLIMINIUM IONS - PREPARATION OF ARACEMIC 2-SUBSTITUTED PIPERIDINES
WANNER, KT
PAINTNER, FF
[J]. TETRAHEDRON, 1994, 50 (10) : 3113 - 3122
[39] Lewis acid-mediated S(N)2 type displacement by Grignard reagents on chiral perhydropyrido[2,1-b]pyrrolo[1,2-d][1,3,4]oxadiazine. Chirality induction in asymmetric synthesis of 2-substituted piperidines
Yamazaki, N
Kibayashi, C
[J]. TETRAHEDRON LETTERS, 1997, 38 (26) : 4623 - 4626
[40] Asymmetric synthesis of substituted cyclopentanes via Michael initiated ring closure reactions
Yechezkel, T
Ghera, E
Ramesh, NG
Hassner, A
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (08) : 2423 - 2436

← 1 2 3 4 →