Ru-catalyzed hydrogenolysis of chiral allylic and propargylic cyclic carbonates: Synthesis of optically active (E)-allylic and allenic alcohols

被引:5
|
作者
Kang, SK
Kim, DY
Rho, HS
Yoon, SH
Ho, PS
机构
[1] Department of Chemistry, Sung Kyun Kwan University, Natural Science Campus
关键词
D O I
10.1080/00397919608003514
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
RuH2(PP3)(4)-catalyzed reductive cleavage reactions of chiral allylic cyclic carbonates with ammonium formate afforded optically active (E)-allylic alcohols with excellent regioselectivity. Alternatively, hydrogenolysis of propargylic cyclic carbonates in the presence of RuH2(PPh(3))(4) catalyst afforded allenic alcohols as a sole products.
引用
收藏
页码:1485 / 1492
页数:8
相关论文
共 50 条
  • [31] PHOSPHINE CATALYZED SYNTHESIS OF UNSATURATED CYCLIC CARBONATES FROM CARBON-DIOXIDE AND PROPARGYLIC ALCOHOLS
    FOURNIER, J
    BRUNEAU, C
    DIXNEUF, PH
    TETRAHEDRON LETTERS, 1989, 30 (30) : 3981 - 3982
  • [32] FACILE SYNTHESIS OF (E)-ALLYLIC ALCOHOLS BY ACID-CATALYZED MODIFICATION OF THE MISLOW-EVANS REARRANGEMENT OF ALLYLIC SULFOXIDES
    MASAKI, Y
    SAKUMA, K
    KAJI, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (06) : 2531 - 2534
  • [33] Recent applications of vinylethylene carbonates in Pd-catalyzed allylic substitution and annulation reactions: Synthesis of multifunctional allylic and cyclic structural motifs
    Khan, Sardaraz
    Ahmad, Tauqir
    Rasheed, Tahir
    Ullah, Nisar
    COORDINATION CHEMISTRY REVIEWS, 2022, 462
  • [34] Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols
    Xie, Jian-Hua
    Zhou, Zhang-Tao
    Kong, Wei-Ling
    Zhou, Qi-Lin
    Journal of the American Chemical Society, 2007, 129 (07): : 1868 - 1869
  • [35] Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols
    Xie, Jian-Hua
    Zhou, Zhang-Tao
    Kong, Wei-Ling
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 1868 - +
  • [36] Synthesis of Optically Active β- or γ-Alkyl-Substituted Alcohols through Copper-Catalyzed Asymmetric Allylic Alkylation with Organolithium Reagents
    Guduguntla, Sureshbabu
    Fananas-Mastral, Martin
    Feringa, Ben L.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17): : 8274 - 8280
  • [37] Copper(II)-catalyzed allylation of propargylic and allylic alcohols by allylsilanes: a facile synthesis of 1,5-enynes
    Yadav, J. S.
    Reddy, B. V. Subba
    Rao, T. Srinivasa
    Rao, K. V. Raghavendra
    TETRAHEDRON LETTERS, 2008, 49 (04) : 614 - 618
  • [38] Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols
    Bickley, JF
    Gillmore, AT
    Roberts, SM
    Skidmore, J
    Steiner, A
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09): : 1109 - 1115
  • [39] A NOVEL-APPROACH TO THE SYNTHESIS OF CHIRAL EPOXIDES AND ALLYLIC ALCOHOLS BY THE USE OF OPTICALLY-ACTIVE PARA-TOLYL SULFINYL GROUP AS A CHIRAL AUXILIARY
    SATOH, T
    OOHARA, T
    YAMAKAWA, K
    TETRAHEDRON LETTERS, 1988, 29 (23) : 2851 - 2854
  • [40] Copper-catalyzed highly enantioselective synthesis of cyclic allylic and homoallylic alcohols with dialkylzinc reagents
    Pineschi, M
    Del Moro, F
    Crotti, P
    Di Bussolo, V
    Macchia, F
    SYNTHESIS-STUTTGART, 2005, (02): : 334 - 337