Diastereoselective Synthesis of γ-Amino Acids and Their Derivatives from Nitroethane via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines Bearing the CH2CH(CO2Me)2 Substituent at C3

被引：17
|
作者：
Sukhorukov, Alexey Yu. [1 ]
Lesiv, Alexey V. [1 ]
Khomutova, Yulia A. [1 ]
Ioffe, Sema L. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
来源：
SYNTHESIS-STUTTGART | 2009年 / 05期
基金：
俄罗斯基础研究基金会;
关键词：
5,6-dihydro-4H-1,2-oxazines; reduction; gamma-amino acids; oxyiminium cations; CONVENIENT PROCEDURE; 6-SILOXY-SUBSTITUTED 5,6-DIHYDRO-4H-1,2-OXAZINES; PYRROLE DERIVATIVES; REDUCTION; HYDROGENATION; DEOXYGENATION; REACTIVITY; ALPHA;
D O I：
10.1055/s-0028-1083360
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective two-step reduction of available 2-[(5,6-dihydro-4H-1,2-oxazin-3-yl)methyl]malonates provides an efficient route to derivatives of different gamma-amino acids. The mechanism and stereochemistry of the first step, reduction of the C=N bond with sodium cyanoborohydride, is discussed.
引用
收藏
页码：741 / 754
页数：14
相关论文
共 50 条
  • [1] A convenient procedure for the synthesis of 3-substituted 5,6-dihydro-4H-1,2-oxazines from nitroethane
    Sukhorukov, Alexey Yu.
    Klenov, Michael S.
    Ivashkin, Pavel E.
    Lesiv, Alexey V.
    Khomutova, Yulya A.
    Ioffe, Sema L.
    SYNTHESIS-STUTTGART, 2007, (01): : 97 - 107
  • [2] Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines
    Tabolin, Andrey A.
    Lesiv, Alexey V.
    Khomutova, Yulia A.
    Ioffe, Sema L.
    SYNTHESIS-STUTTGART, 2012, 44 (12): : 1898 - 1906
  • [3] AN EFFICIENT AND SIMPLE SYNTHESIS OF 3,4,5,6-TETRAHYDRO-2H-1,2-OXAZINES BY SODIUM CYANOBOROHYDRIDE REDUCTION OF 5,6-DIHYDRO-4H-1,2-OXAZINES
    ZIMMER, R
    ARNOLD, T
    HOMANN, K
    REISSIG, HU
    SYNTHESIS-STUTTGART, 1994, (10): : 1050 - 1056
  • [4] SYNTHESIS OF PYRROLE DERIVATIVES FROM 5,6-DIHYDRO-4H-1,2-OXAZINES VIA REDUCTIVE DEOXYGENATION BY USE OF FE3(CO)12
    NAKANISHI, S
    OTSUJI, Y
    ITOH, K
    HAYASHI, N
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (12) : 3595 - 3600
  • [5] Catalytic hydrogenation of 5,6-dihydro-4H-1,2-oxazines bearing a functionalized methylene group at C-3
    Sukhorukov, Alexey Yu.
    Lesiv, Alexey V.
    Eliseev, Oleg L.
    Khomutova, Yulia A.
    Ioffe, Sema L.
    Borissova, Alexandra O.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (23) : 4025 - 4034
  • [6] Stereoselective Synthesis of Unnatural β-Amino Acids from Nitroethane via 5,6-Dihydro-4H-1,2-oxazin-3-ylacetates
    Sukhorukov, Alexey Yu.
    Lesiv, Alexey V.
    Eliseev, Oleg L.
    Khomutova, Yulia A.
    Ioffe, Sema L.
    SYNTHESIS-STUTTGART, 2009, (15): : 2570 - 2578
  • [7] Synthesis of Substituted 5-(3-Hydroxypropyl)pyrrolidin-2-ones and Pyrrolizidinones from Nitroethane via C3 Functionalized 5,6-Dihydro-4H-1,2-oxazines: A Novel Approach to Some Analogues of the Antidepressant Rolipram
    Sukhorukov, Alexey Yu
    Lesiv, Alexey V.
    Khomutova, Yulia A.
    Ioffe, Sema L.
    Tartakovsky, Vladimir A.
    SYNTHESIS-STUTTGART, 2009, (12): : 1999 - 2008
  • [8] A new course of reduction of substituted 5,6-dihydro-4H-1 2-oxazines to furan derivatives
    Sukhorukov, Alexey Yu.
    Lesiv, Alexei V.
    Eliseev, Oleg L.
    Khomutova, Yuliya A.
    Bondarenko, Tatyana N.
    Lapidus, Albert L.
    Ioffe, Sema L.
    MENDELEEV COMMUNICATIONS, 2007, 17 (02) : 122 - 124
  • [9] SYNTHESIS WITH 1,2-OXAZINES .2. SYNTHESIS AND PROPERTIES OF 2,3-DIMETHYL-5,6-DIHYDRO-4H-1,2-OXAZINIUMIODIDE
    HARDEGGER, B
    SHATZMILLER, S
    HELVETICA CHIMICA ACTA, 1976, 59 (08) : 2765 - 2767
  • [10] Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines
    Tabolin, Andrey A.
    Lesiv, Alexey V.
    Khomutova, Yulia A.
    Nelyubina, Yulia V.
    Ioffe, Sema L.
    TETRAHEDRON, 2009, 65 (23) : 4578 - 4592
12345