Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines

被引：9
|
作者：
Gawley, RE [1 ]
Barolli, G
Madan, S
Saverin, M
O'Connor, S
机构：
[1] Univ Miami, Dept Chem, Coral Gables, FL 33124 USA
[2] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 08期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
(stannanyl)pyrrolidines; TCC; N-acyliminium ion; asymmetric synthesis;
D O I：
10.1016/j.tetlet.2003.12.080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
trans-Cumylcyclohexanol (TCC) is used as a chiral auxiliary for the stereoselective addition of tributyltinlithium to N-acylpyrrolidinium/piperidinium ion with 70-80% diastereoselectivity at 0degreesC. After removal of the minor diastereomer by radial chromatography, enantiopure N-methyl-2-(tributylstannyl)pyrrolidine and piperidine were produced by reductive removal of the auxiliary. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1759 / 1761
页数：3
相关论文
共 50 条
  • [31] Oxidation of 2-substituted pyrrolidines and piperidines as nicotine analogues
    Moehrle, Hans
    Berlitz, Johannes
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2008, 63 (08): : 985 - 992
  • [32] Boron(III) bromide-induced ring contraction of 3-oxygenated piperidines to 2-(bromomethyl)pyrrolidines
    Tehrani, KA
    Van Syngel, K
    Boelens, M
    Contreras, J
    De Kimpe, N
    Knight, DW
    TETRAHEDRON LETTERS, 2000, 41 (14) : 2507 - 2510
  • [33] Diastereoselective synthesis of 2,4,5-trisubstituted piperidines from enantiopure β-amino esters
    Ma, DW
    Sun, HY
    TETRAHEDRON LETTERS, 1999, 40 (18) : 3609 - 3612
  • [34] Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols
    Tiecco, Marcello
    Testaferri, Lorenzo
    Bagnoli, Luana
    Scarponi, Catalina
    Temperini, Andrea
    Marini, Francesca
    Santi, Claudio
    TETRAHEDRON-ASYMMETRY, 2007, 18 (23) : 2758 - 2767
  • [35] Synthesis of enantiopure trisubstituted piperidines from a chiral epoxyaziridine and α-amino esters
    Ochoa-Teran, Adrian
    Concellon, Jose M.
    Rivero, Ignacio. A.
    ARKIVOC, 2009, : 288 - 297
  • [36] The Asymmetric Aza-silyl-Prins Reaction: Synthesis of Enantiopure Piperidines
    Mittapalli, Ramana R.
    Guesne, Sebastien J. J.
    Parker, Robert J.
    Klooster, Wim T.
    Coles, Simon J.
    Skidmore, John
    Dobbs, Adrian P.
    ORGANIC LETTERS, 2019, 21 (02) : 350 - 355
  • [37] Enantioenriched 2-(metalated)-pyrrolidines
    Seelhammer, G
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U120 - U120
  • [38] ENANTIOSPECIFIC SYNTHESIS OF N-BENZYL-2-ALKYL PYRROLIDINES AND PIPERIDINES MEDIATED BY CHIRAL ORGANOBORANE REAGENTS
    NGUYEN, T
    SHERMAN, D
    BALL, D
    SOLOW, M
    SINGARAM, B
    TETRAHEDRON-ASYMMETRY, 1993, 4 (02) : 189 - 192
  • [39] A GENERAL STEREOCONTROLLED SYNTHESIS OF CIS-2,3 DISUBSTITUTED PYRROLIDINES AND PIPERIDINES
    PAL, K
    BEHNKE, ML
    TONG, LA
    TETRAHEDRON LETTERS, 1993, 34 (39) : 6205 - 6208
  • [40] Synthesis of enantiopure 3,4-disubstituted piperidines. An asymmetric synthesis of (+)-paroxetine
    Amat, M
    Hidalgo, J
    Bosch, J
    TETRAHEDRON-ASYMMETRY, 1996, 7 (06) : 1591 - 1594
12345