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
  • [1] UTILIZATION OF PHOSPHORUS SYNTHETIC EQUIVALENTS OF ALLYLIC GAMMA-FUNCTIONALIZED CARBOCATIONS - SYNTHESIS OF FUNCTIONALIZED ALKENES
    CRISTAU, HJ
    ALHAMAD, AK
    TORREILLES, E
    COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II, 1992, 314 (13): : 1423 - 1428
  • [2] Advances in synthesis of chiral allylic amines
    Luo, Jie
    Jiang, Huan-Feng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (02) : 187 - 193
  • [3] A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF ALLYLIC AND HOMOALLYLIC AMINES
    DESHONG, P
    LEGINUS, JM
    LANDER, SW
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04): : 574 - 576
  • [4] Synthesis of ?,?-Chiral Trifluoromethylated Amines through the Stereospecific Isomerization of ?-Chiral Allylic Amines
    Garcia-Vazquez, Victor
    Martinez-Pardo, Pablo
    Postole, Alexandru
    Inge, A. Ken
    Martin-Matute, Belen
    ORGANIC LETTERS, 2022, 24 (21) : 3867 - 3871
  • [5] PREPARATION AND USE OF GAMMA-FUNCTIONALIZED BETA-KETOPHOSPHORANES IN SYNTHESIS
    LECORRE, M
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1974, (9-10): : 1951 - 1955
  • [6] A SIMPLE METHOD FOR THE SYNTHESIS OF GAMMA-FUNCTIONALIZED VINYL SULFONES AND ALLYL SULFONES
    NAJERA, C
    PEREZPINAR, A
    SANSANO, JM
    TETRAHEDRON, 1991, 47 (32) : 6337 - 6352
  • [7] Stereoselective synthesis of dipeptidomimetics using chiral allylic aziridines
    Larsson, E
    Berts, W
    Luthman, K
    PEPTIDES FOR THE NEW MILLENNIUM, 2000, : 155 - 156
  • [8] Stereoselective synthesis of allylic amines by rearrangement of allylic trifluoroacetimidates:: stereoselective synthesis of polyoxamic acid and derivatives of other α-amino acids
    Savage, I
    Thomas, EJ
    Wilson, PD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (22): : 3291 - 3303
  • [9] CHIRAL OXAZOLIDINES AS TEMPLATES FOR STEREOSELECTIVE SYNTHESIS OF CHIRAL HOMOALLYL AMINES
    WU, MJ
    PRIDGEN, LN
    SYNLETT, 1990, (10) : 636 - 637
  • [10] PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF ALLYLIC AMINES
    TAMARU, Y
    BANDO, T
    KAWAMURA, Y
    OKAMURA, K
    YOSHIDA, Z
    SHIRO, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (20) : 1498 - 1500
12345