ASYMMETRIC 1,4-ADDITIONS TO GAMMA-MENTHYLOXYBUTENOLIDES .2. ENANTIOSELECTIVE SYNTHESIS OF LIGNAN TYPE COMPOUNDS

被引:12
|
作者
JANSEN, JFGA [1 ]
JANSEN, C [1 ]
FERINGA, BL [1 ]
机构
[1] UNIV GRONINGEN,DEPT ORGAN CHEM,NIJENBORGH 16,9747 AG GRONINGEN,NETHERLANDS
关键词
D O I
10.1016/S0957-4166(00)80529-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Addition of dithianes, derived from alkyl- and aryl-aldehydes, to (5R)-menthyloxy-2[5H]-furanone followed by quenching with substituted benzylhalides or a benzaldehyde gives enantiomerically pure lignan type compounds in good yields.
引用
收藏
页码:109 / 110
页数:2
相关论文
共 50 条
  • [41] Catalytic Asymmetric Synthesis of 2,6-Disubstituted Cuneanes through Enantioselective Constitutional Isomerization of 1,4-Disubstituted Cubanes
    Takebe, Hiyori
    Matsubara, Seijiro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (37)
  • [42] Using the same organocatalyst for asymmetric synthesis of both enantiomers of glutamic acid-derived Ni(II) complexes via 1,4-additions of achiral glycine and dehydroalanine Schiff base Ni(II) complexes
    Yuri N. Belokon
    Zalina T. Gugkaeva
    Karine V. Hakobyan
    Victor I. Maleev
    Margarita A. Moskalenko
    Victor N. Khrustalev
    Ashot S. Saghyan
    Alan T. Tsaloev
    Kiryl K. Babievsky
    Amino Acids, 2012, 43 : 299 - 308
  • [43] Synthesis of Sulfur-Substituted α-Stereogenic Amides and Ketones: Highly Enantioselective Sulfa-Michael Additions of 1,4-Dicarbonylbut-2-enes
    Zhao, Fangli
    Zhang, Wen
    Yang, Yuanyong
    Pan, Yuanhang
    Chen, Wenchao
    Liu, Hongjun
    Yan, Lin
    Tan, Choon-Hong
    Jiang, Zhiyong
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) : 2624 - 2630
  • [44] SYNTHESIS OF POLYCYCLIC COMPOUNDS .2. THE RING CLOSURE OF BETA-CARBOXY-GAMMA-1-NAPHTHYLBUTYRIC ACID
    BARDHAN, JC
    NASIPURI, D
    ADHYA, RN
    JOURNAL OF THE CHEMICAL SOCIETY, 1956, (FEB): : 355 - 358
  • [45] Carbon-carbon bond-forming enantioselective synthesis of chiral organosilicon compounds by rhodium/chiral diene-catalyzed asymmetric 1,4-addition reaction
    Shintani, R
    Okamoto, K
    Hayashi, T
    ORGANIC LETTERS, 2005, 7 (21) : 4757 - 4759
  • [46] FRIEDEL-CRAFTS REACTIONS WITH GAMMA-VALEROLACTONE .2. A SYNTHESIS OF 1-METHYL-ANTHRACENES AND 1,4-DIMETHYL-ANTHRACENES
    MOSBY, WL
    JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (08): : 964 - 970
  • [47] SYNTHETIC STUDIES ON AROMADENDRANE-TYPE COMPOUNDS .2. STEREOSELECTIVE SYNTHESIS OF (+)-1,2-DIDEHYDROAROMADENDRANE
    TANAKA, T
    FUNAKOSHI, Y
    UENAKA, K
    MAEDA, K
    MIKAMIYAMA, H
    IWATA, C
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (06) : 1243 - 1246
  • [48] SYNTHESIS AND ANALGESIC ACTIVITY OF SOME COMPOUNDS RELATED TO PROPOXYPHENE .2. SELECTIVE RING OPENING OF AN ASYMMETRIC EPOXIDE WITH ISOBUTENYLLITHIUM - AN ALTERNATIVE SYNTHESIS OF GAMMA-SUBSTITUTED ALLYL CARBINOLS
    DONETTI, A
    MANTEGANI, A
    MARAZZIU.E
    FARMACO-EDIZIONE SCIENTIFICA, 1970, 25 (07): : 500 - +
  • [49] SYNTHESIS OF FORMAZANS WITH LUMINESCENT GROUPS .2. SYNTHESIS OF 1,2,3,4-TETRAHYDRO-1,4-DIOXOPHTHALAZIN-5-YL SULFAMOYLFORMAZAN AND INTERMEDIATE SULFONAMIDO COMPOUNDS
    OSTROVSKAYA, VM
    ZARIPOVA, TA
    LUSHINA, OT
    ZHURNAL ORGANICHESKOI KHIMII, 1976, 12 (06): : 1347 - 1351
  • [50] ASYMMETRIC ALPHA-SUBSTITUTED PHENETHYLAMINES .2. THE ENANTIOSELECTIVE SYNTHESIS OF 1-ARYL-2-PHENYLETHYLAMINES FROM I-AMINO AND D-AMINO ACIDS BY MEANS OF 1,3-ASYMMETRIC INDUCTION
    SUZUKI, Y
    TAKAHASHI, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1983, 31 (01) : 31 - 40