DIASTEREOSELECTIVE CONJUGATE ADDITION OF AMMONIA IN THE SYNTHESIS OF CHIRAL PYRROLIDINES

被引:21
|
作者
ROBINA, I [1 ]
GEARING, RP [1 ]
BUCHANAN, JG [1 ]
WIGHTMAN, RH [1 ]
机构
[1] HERIOT WATT UNIV,DEPT CHEM,EDINBURGH EH14 4AS,MIDLOTHIAN,SCOTLAND
关键词
D O I
10.1039/p19900002622
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
threo-Selectivity in the conjugate addition of ammonia to 4,5-isopropylidenedioxypent-2-enoic esters has been exploited in a new synthesis of homochiral pyrrolidines; the origin of the diastereoselectivity is discussed.
引用
收藏
页码:2622 / 2624
页数:3
相关论文
共 50 条
  • [31] Chiral Cyclobutane Synthesis by Exploiting a Heteroatom-Directed Conjugate Addition
    Tsao, Kuo-Wei
    Isobe, Minoru
    ORGANIC LETTERS, 2010, 12 (22) : 5338 - 5341
  • [32] Advances in Synthesis of Enantioenriched Chiral Sulfones by Enantioselective Conjugate Addition Reactions
    Liang, Xiayu
    Shen, Yongcun
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (01)
  • [33] ASYMMETRIC CONJUGATE ADDITIONS TO CHIRAL BICYCLIC LACTAMS - SYNTHESIS OF ARACEMIC TRANS - 2, 3 - DISUBSTITUTED PYRROLIDINES
    MEYERS, AI
    SNYDER, LB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 142 - ORGN
  • [34] Diastereoselective addition of functionalized organolithium compounds to (-)-menthone - synthesis of chiral ligands for enantioselective addition of diethylzinc to aldehydes
    Zagranyarska, I.
    Kostova, K.
    Chimov, A.
    Dimitrov, V.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2017, 49 : 10 - 17
  • [35] Diastereoselective zinc-catalyzed conjugate addition of alkynes
    Knöpfel, TF
    Boyall, D
    Carreira, EM
    ORGANIC LETTERS, 2004, 6 (13) : 2281 - 2283
  • [36] DIASTEREOSELECTIVE CONJUGATE ADDITION APPROACH TO PICENADOL AND OXYGENATED ANALOGS
    MARTINELLI, MJ
    PETERSON, BC
    HUTCHISON, DR
    HETEROCYCLES, 1993, 36 (09) : 2087 - 2097
  • [37] 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
  • [38] Conjugate addition of nitroalkanes to N-substituted maleimides.: Synthesis of 3-alkylsuccinimides and pyrrolidines
    Ballini, R
    Bosica, G
    Cioci, G
    Fiorini, D
    Petrini, M
    TETRAHEDRON, 2003, 59 (20) : 3603 - 3608
  • [39] Hydroxy alkenenitriles: Diastereoselective conjugate addition-alkylations
    Fleming, FF
    Wang, QZ
    Steward, OW
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11): : 4235 - 4238
  • [40] Asymmetric multicomponent reactions: Diastereoselective synthesis of substituted pyrrolidines and prolines
    Ghosh, Arun K.
    Kulkarni, Sarang
    Xu, Chun-Xiao
    Fanwick, Phillip E.
    ORGANIC LETTERS, 2006, 8 (20) : 4508 - 4511