Diastereoselective addition of organotitanium reagents to chiral γ-hydroxybutenolides

被引:0
|
作者
Miles, William H. [1 ]
Duca, Daniela G. [1 ]
Freedman, Jaryd T. [1 ]
Goodzeit, Elliot O. [1 ]
Hamman, Kristin B. [1 ]
De Sousa, Chiquita A. Palha [1 ]
Selfridge, Brandon R. [1 ]
机构
[1] Lafayette Coll, Dept Chem, Easton, PA 18042 USA
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of (i-PrO)(3)TiCH3 to gamma-hydroxybutenolides having a chiral center with an alkoxy group adjacent to the ketone functionality (of the open chain form) gave gamma-lactones in good yields and high diastereoselectivity.
引用
收藏
页码:195 / 198
页数:4
相关论文
共 50 条
  • [41] Inverse Temperature Dependence in the Diastereoselective Addition of Grignard Reagents to a Tetrahydrofurfural
    Mowat, Jeffrey
    Kang, Baldip
    Fonovic, Branden
    Dudding, Travis
    Britton, Robert
    ORGANIC LETTERS, 2009, 11 (10) : 2057 - 2060
  • [42] DIASTEREOSELECTIVE ADDITION OF VINYL ORGANOMETALLIC REAGENTS TO L-SERINAL
    COLEMAN, RS
    CARPENTER, AJ
    TETRAHEDRON LETTERS, 1992, 33 (13) : 1697 - 1700
  • [43] Diastereoselective allylation of a chiral imine with allylzinc reagents: Diastereoselective synthesis of a novel broad spectrum carbapenem
    Sugimoto, Y
    Imamura, H
    Sakoh, H
    Yamada, K
    Morishima, H
    SYNLETT, 2001, (11) : 1747 - 1750
  • [44] Asymmetric synthesis of diarylmethylamines by diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines:: switchover of diastereofacial selectivity
    Plobeck, N
    Powell, D
    TETRAHEDRON-ASYMMETRY, 2002, 13 (03) : 303 - 310
  • [45] HIGHLY DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL IMINES DERIVED FROM 1-(2-METHOXYPHENYL)ETHYLAMINE
    HASHIMOTO, Y
    KOBAYASHI, N
    KAI, A
    SAIGO, K
    SYNLETT, 1995, (09) : 961 - &
  • [46] DIASTEREOSELECTIVE ADDITION OF ALLYL CUPRATES TO UNSATURATED CHIRAL IMIDES
    POURCELOT, G
    MELNYK, O
    BESACE, Y
    STEPHAN, E
    CRESSON, P
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 388 (1-2) : C5 - C8
  • [47] DIASTEREOSELECTIVE CONJUGATE ADDITION OF AMMONIA IN THE SYNTHESIS OF CHIRAL PYRROLIDINES
    ROBINA, I
    GEARING, RP
    BUCHANAN, JG
    WIGHTMAN, RH
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09): : 2622 - 2624
  • [48] Highly diastereoselective addition of silyldihalomethyllithiums to chiral alkyl esters
    Shinokubo, H
    Kondo, J
    Inoue, A
    Oshima, K
    CHIRALITY, 2003, 15 (01) : 31 - 37
  • [49] Diastereoselective addition reactions of racemic chiral vinyl sulfimides
    Rayner, Charlotte P.
    Clark, Andrew J.
    Rooke, Stuart M.
    Sparey, Tim J.
    Taylor, Paul C.
    Journal of the Chemical Society, Perkin Transactions 1, 2000, (01): : 79 - 87
  • [50] ORGANOTITANIUM REAGENTS AID ALDEHYDE ADDITIONS
    STINSON, S
    CHEMICAL & ENGINEERING NEWS, 1989, 67 (22) : 25 - 27