Stereocontrolled α-alkylation of oxime ether derived from terpene:: Efficient synthesis of new chiral γ- and δ-amino alcohols

被引:8
|
作者
Jennequin, Thomas [2 ]
Labat, Stephane [2 ]
Toupet, Loic [3 ]
Caille, Jean-Claude [1 ]
Mauduit, Marc [2 ]
机构
[1] Zambon ZI Croix Cadeau, F-49243 Avrille, France
[2] Ecole Natl Super Chim Rennes, Equipe Chim Org & Supramol, CNRS, UMR 6226, F-35700 Rennes, France
[3] CNRS, UMR 6626, Grp Matiere Condensee & Mat, F-35042 Rennes, France
关键词
oxime ether; (+)-nopinone; stereocontrolled alkylation; amino alcohols;
D O I
10.1055/s-2008-1078492
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The alkylation of (+)-nopinone oxime ether with various electrophiles afforded the corresponding adduct with a total stereoselectivity. Further reduction of the oxime ether afforded an easily access to new chiral gamma-and delta-amino alcohols of high interest for catalysis and asymmetric synthesis.
引用
收藏
页码:1669 / 1672
页数:4
相关论文
共 50 条
  • [1] STEREOCONTROLLED CATALYTIC ASYMMETRIC REDUCTION OF KETONES WITH OXAZABOROLIDINES DERIVED FROM NEW CHIRAL AMINO-ALCOHOLS
    KIM, YH
    PARK, DH
    BYUN, IS
    YOON, IK
    PARK, CS
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17): : 4511 - 4512
  • [2] A new stereocontrolled synthesis of amino alcohols from organoboronic acids
    Petasis, NA
    Zavialov, IA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 56 - ORGN
  • [3] Synthesis of glycidyl ethers derived from terpene α-amino oximes and β-substituted alcohols on their basis
    T. A. Shumilova
    A. M. Agafontsev
    A. V. Tkachev
    Russian Chemical Bulletin, 2015, 64 : 99 - 106
  • [4] Synthesis of glycidyl ethers derived from terpene α-amino oximes and β-substituted alcohols on their basis
    Shumilova, T. A.
    Agafontsev, A. M.
    Tkachev, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2015, 64 (01) : 99 - 106
  • [5] Synthesis of new chiral amino ether derivatives:: synthetic application of meso aziridinium ions prepared from β-amino alcohols
    Periasamy, M
    Seenivasaperumal, M
    Rao, VD
    TETRAHEDRON-ASYMMETRY, 2004, 15 (24) : 3847 - 3852
  • [6] Enantioselective alkynylations of aromatic and aliphatic aldehydes catalyzed by terpene derived chiral amino alcohols
    Watts, CC
    Thoniyot, P
    Hirayama, LC
    Romano, T
    Singaram, B
    TETRAHEDRON-ASYMMETRY, 2005, 16 (10) : 1829 - 1835
  • [7] Cesium promoted O-alkylation of alcohols for the efficient ether synthesis
    Dueno, EE
    Chu, FX
    Kim, SI
    Jung, KW
    TETRAHEDRON LETTERS, 1999, 40 (10) : 1843 - 1846
  • [8] Efficient access to new chiral ferrocenyl γ-lactams from amino alcohols
    Soueidan, Mohamad
    Jida, Mouhamad
    Bousquet, Till
    Niedercorn, Francine Agbossou
    Pelinski, Lydie
    NEW JOURNAL OF CHEMISTRY, 2011, 35 (05) : 991 - 993
  • [9] Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene
    Kmieciak, Anna
    Krzeminski, Marek P.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 2493 - 2499
  • [10] Synthesis of chiral, nonracemic methyleneaziridines derived from beta-amino alcohols
    Ince, J
    Ross, TM
    Shipman, M
    Ennis, DS
    TETRAHEDRON-ASYMMETRY, 1996, 7 (12) : 3397 - 3406