Stereoselective synthesis of new enantiomerically enriched N-protected γ-amino acetylenic esters.

被引：11
|
作者：
Reginato, G [1 ]
Mordini, A
Capperucci, A
Degl'Innocenti, A
Manganiello, S
机构：
[1] CNR, Ctr Chim & Struttura Composti Eterociclici & Loro, I-00185 Rome, Italy
[2] Dipartimento Chim Organ U Schiff, I-50121 Florence, Italy
来源：
TETRAHEDRON | 1998年 / 54卷 / 34期
关键词：
alkynes; amino acids and derivatives; amino aldehydes; carboxylation;
D O I：
10.1016/S0040-4020(98)00623-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new class of differently protected chiral gamma-amino acetylenic esters have been synthesized using natural occuring amino acids as chiral source. Enantiomerically enriched propargylamines or vinyldibromides have been treated with BuLi at low temperature affording, after carboxylation, enantiomerically enriched derivatives of alkynologous amino esters. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：10217 / 10226
页数：10
相关论文
共 50 条
  • [41] REGIOSELECTIVE SYNTHESIS OF ISOPROPENYL ESTERS BY RUTHENIUM CATALYZED ADDITION OF N-PROTECTED AMINO-ACIDS TO PROPYNE
    RUPPIN, C
    DIXNEUF, PH
    LECOLIER, S
    TETRAHEDRON LETTERS, 1988, 29 (42) : 5365 - 5368
  • [42] Tin(II) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement
    Bandyopadhyay, Anupam
    Agrawal, Neha
    Mali, Sachitanand M.
    Jadhav, Sandip V.
    Gopi, Hosahudya N.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (21) : 4855 - 4860
  • [43] USE OF ETHOXYACETYLENE FOR SYNTHESIS OF N-PROTECTED AMINO-ACIDS
    BANKS, GR
    COHEN, D
    PATTENDE.GE
    THOMAS, JAG
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (02): : 126 - &
  • [44] INVESTIGATION ON RACEMIZATION OF ORTHO METHOXYPHENYL ESTERS OF N-PROTECTED AMINO-ACIDS
    BANKOWSKI, K
    DRABAREK, S
    ROCZNIKI CHEMII, 1972, 46 (04): : 607 - +
  • [45] A new approach to β-amino acids:: biotransformation of N-protected β-amino nitriles
    Preiml, M
    Hillmayer, K
    Klempier, N
    TETRAHEDRON LETTERS, 2003, 44 (27) : 5057 - 5059
  • [46] A SIMPLE METHOD FOR THE PREPARATION OF DIPHENYLMETHYL ESTERS OF N-PROTECTED AMINO-ACIDS
    LAPATSANIS, L
    MILIAS, G
    PARASKEWAS, S
    SYNTHESIS-STUTTGART, 1985, (05): : 513 - 515
  • [47] A SIMPLE SYNTHESIS OF N-PROTECTED AMINO-ACID AMIDES
    BOOMGAARDEN, M
    HEINRICH, G
    HENKLEIN, P
    PHARMAZIE, 1992, 47 (09): : 710 - 711
  • [48] Biocatalytic production of unnatural amino acids, mono esters and N-protected derivatives
    Fotheringham, IG
    Pantaleone, DP
    Taylor, PP
    CHIMICA OGGI-CHEMISTRY TODAY, 1997, 15 (9-10) : 33 - 37
  • [49] CONVENIENT SYNTHESIS OF N-PROTECTED AMINO-ACID AMIDES
    NOZAKI, S
    MURAMATSU, I
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (07) : 2647 - 2648
  • [50] HYDROLYSIS OF N-PROTECTED AMINO-ACID ALLYL ESTERS BY ENZYMATIC CATALYSIS
    XAUS, N
    CLAPES, P
    BARDAJI, E
    TORRES, JL
    JORBA, X
    MATA, J
    VALENCIA, G
    BIOTECHNOLOGY LETTERS, 1989, 11 (06) : 393 - 396
12345