A new stereoselective synthesis of chiral gamma-functionalized (E)-allylic amines

被引：49
|
作者：
Reginato, G
Mordini, A
Messina, F
Degl'Innocenti, A
Poli, G
机构：
[1] CNR-Centro di Stud. Sulla Chim. e S., Dipto. di Chimica Organica U. Schiff, 50121 Firenze
来源：
TETRAHEDRON | 1996年 / 52卷 / 33期
关键词：
D O I：
10.1016/0040-4020(96)00617-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral t-Boc protected propargylic amines have been obtained starting from aminoaldehydes derived from natural aminoacids. Stannylcupration of these substrates affords an easy regio- and stereocontrolled route to the corresponding gamma-stannylated (E)-allylamines which are useful intermediates for the synthesis of the corresponding gamma-funtionalized allylic systems. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：10985 / 10996
页数：12
相关论文
共 50 条
  • [31] Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines
    Prudel, Cynthia
    Huwig, Kai
    Kazmaier, Uli
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (14) : 3181 - 3188
  • [32] STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED OLEFINS - ORTHOESTER CLAISEN REARRANGEMENT OF ALKYNYL ALLYLIC ALCOHOLS
    PARKER, KA
    KOSLEY, RW
    TETRAHEDRON LETTERS, 1975, (09) : 691 - 694
  • [33] Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines
    Prudel, Cynthia
    Huwig, Kai
    Kazmaier, Uli
    Chemistry - A European Journal, 2020, 26 (14): : 3181 - 3188
  • [34] Environmentally Benign Regio- and Stereoselective Synthesis of Functionalized Tertiary Amines
    Wang Rendong
    Li Jian
    Li Chunju
    Liu Jun
    Li Dafeng
    Jia Xueshun
    Zhai Hongbin
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (07) : 1253 - 1256
  • [35] ENANTIOSELECTIVE CATALYTIC ADDITION OF FUNCTIONALIZED DIALKYLZINC COMPOUNDS TO BETA-STANNYLATED ALDEHYDES - A CONVENIENT PREPARATION OF CHIRAL BETA-FUNCTIONALIZED AND GAMMA-FUNCTIONALIZED SECONDARY ALCOHOLS
    BRIEDEN, W
    OSTWALD, R
    KNOCHEL, P
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04): : 582 - 584
  • [36] A Convenient, Highly Stereoselective, Metal-Free Synthesis of Chiral Amines
    Guizzetti, Stefania
    Benaglia, Maurizio
    Biaggi, Cinzia
    Celentano, Giuseppe
    SYNLETT, 2010, (01) : 134 - 136
  • [37] On the utility of S-mesitylsulfinimines for the stereoselective synthesis of chiral amines and aziridines
    Roe, Caroline
    Sola, Toni Moragas
    Sasraku-Neequaye, Leonid
    Hobbs, Heather
    Churcher, Ian
    MacPherson, David
    Stockman, Robert A.
    CHEMICAL COMMUNICATIONS, 2011, 47 (26) : 7491 - 7493
  • [38] ASYMMETRIC DIELS-ALDER REACTIONS WITH GAMMA-FUNCTIONALIZED ALPHA,BETA-UNSATURATED CHIRAL N-ACYLOXAZOLIDINONES - SYNTHESIS OF (+)-S-145
    MARTINELLI, MJ
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17): : 5065 - 5073
  • [39] CARBOHYDRATES AS CHIRAL TEMPLATES - STEREOSELECTIVE SYNTHESIS OF CHIRAL HOMOALLYL AMINES AND BETA-AMINO ACIDS
    LASCHAT, S
    KUNZ, H
    SYNLETT, 1990, (01) : 51 - 52
  • [40] STEREOSELECTIVE TOTAL SYNTHESIS OF BENGAMIDE-E FROM GLYCERALDEHYDE ACETONIDE AND A NONRACEMIC GAMMA-ALKOXY ALLYLIC STANNANE
    MARSHALL, JA
    LUKE, GP
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23): : 6229 - 6234
12345