HIGHLY REGIOSELECTIVE, (E)-STEREOSELECTIVE AND DIASTEREOSELECTIVE SN2' ADDITION OF ORGANOCUPRATES TO CHIRAL ALLYLIC CYCLIC CARBONATES

被引：25
作者：
KANG, SK
LEE, DH
SIM, HS
LIM, JS
机构：
[1] Department of Chemistry, Sung Kyun Kwan University, Suwon, 440-746, Natural Science Campus
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 01期
关键词：
D O I：
10.1016/S0040-4039(00)60065-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of the cyclic carbonates of acyclic vinyl diols with RCu(CN)Li.BF3, RCu(CN)MgBr-BF3, or RMgBr.CuI (cat) in THF at -78-degrees-C proceeded in S(N)2' fashion and resulted in the formation of alkylated (E)-allylic alcohols with remarkably high diastereoselectivity. This reaction represents an efficient 1, 3-chirality transfer method.
引用
收藏
页码：91 / 94
页数：4
相关论文
共 50 条
  • [41] Sequential Nucleophilic Addition/Intramolecular Cycloaddition to Chiral Nonracemic Cyclic Nitrones: A Highly Stereoselective Approach to Polyhydroxynortropane Alkaloids
    Delso, Ignacio
    Tejero, Tomas
    Goti, Andrea
    Merino, Pedro
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) : 4139 - 4143
  • [42] Copper-Mediated SN2′ Allyl-Alkyl and Allyl-Boryl Couplings of Vinyl Cyclic Carbonates
    Miralles, Nuria
    Enrique Gomez, Jose
    Kleij, Arjan W.
    Fernandez, Elena
    ORGANIC LETTERS, 2017, 19 (22) : 6096 - 6099
  • [43] ORGANOCUPRATE INDUCED SN2'-TYPE REACTIONS OF ALLYLIC ETHERS OF BENZOTHIAZOLE - NEW, SELECTIVE SYNTHESIS OF (E)-ALKENOLS
    CALO, V
    LOPEZ, L
    MARCHESE, G
    PESCE, G
    SYNTHESIS-STUTTGART, 1979, (11): : 885 - 887
  • [44] Highly diastereoselective and enantioselective addition of organometallic reagents to a chiral C2-symmetrical bisimine
    Sun, XX
    Wan, SJ
    Sun, SJ
    Zhu, J
    Deng, JG
    SYNLETT, 2005, (18) : 2776 - 2780
  • [45] Highly Stereocontrolled Formal Synthesis of Brassinolide via Chiral Sulfoxide-Directed SN2' Reactions
    Marino, J. P.
    De Dios, A.
    Anna, L. J.
    Fernandez De la Pradilla, R.
    Journal of Organic Chemistry,
  • [46] Synthetic Studies on Taxol: Highly Stereoselective Construction of the Taxol C-Ring via SN2′ Reduction of an Allylic Phosphonium Salt (vol 8, pg 2973, 2006)
    Utsugi, Masayuki
    Miyano, Masayuki
    Nakada, Masahisa
    ORGANIC LETTERS, 2014, 16 (05) : 1533 - 1533
  • [47] Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chlorosugar
    Bag, Subhendu Sekhar
    Talukdar, Sangita
    Anjali, S. J.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (08) : 2044 - 2050
  • [48] COPPER-CATALYZED REACTIONS OF ORGANOTITANIUM REAGENTS - HIGHLY SELECTIVE SN2'-ALLYLATION AND CONJUGATE ADDITION
    ARAI, M
    LIPSHUTZ, BH
    NAKAMURA, E
    TETRAHEDRON, 1992, 48 (27) : 5709 - 5718
  • [49] Highly Diastereoselective Conjugate Addition-Elimination of Chiral Nickel(II) Glycinate with Activated Allylic Acetates for Asymmetric Synthesis of Glutamic Acid Derivatives
    Wang, Jiang
    Shi, Jianmei
    Zhang, Xiaodong
    Lin, Daizong
    Jiang, Hualiang
    Liu, Hong
    SYNTHESIS-STUTTGART, 2009, (10): : 1744 - 1752
  • [50] A highly diastereoselective dioxetane formation by the hydroxy-directed [2+2] cycloaddition of singlet oxygen to a chiral allylic alcohol
    Adam, W
    Saha-Möller, CR
    Schambony, SB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1834 - 1838
12345