Acyclic stereocontrol in the Ireland-Claisen rearrangement of α-branched esters

被引：79
|
作者：
Qin, Ying-Chuan [1 ]
Stivala, Craig. E. [1 ]
Zakarian, Armen [1 ]
机构：
[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 39期
关键词：
chiral amines; diastereoselectivity; enolization; Ireland-Claisen rearrangement; synthetic methods;
D O I：
10.1002/anie.200702142
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) To overcome the limitation of the poor diastereoselectivity of the title reaction with α-branched esters, chiral amides were used to generate the enolate intermediates diastereoselectively. The desired rearrangement then took place with efficient transfer of chirality to give densely functionalized products with at least one quaternary stereocenter (see scheme; PMB, TBS, and TBDPS are protecting groups). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：7466 / 7469
页数：4
相关论文
共 50 条
  • [41] Enantioselective total synthesis of Β-elemene and fuscol based on enantiocontrolled Ireland-claisen rearrangement
    Corey, E.J.
    Roberts, B.E.
    Dixon, B.R.
    Journal of the American Chemical Society, 1995, 117 (01)
  • [42] Unprecedented alkene stereocontrol in the Claisen rearrangement of cyclic bis-allylic esters
    McFarland, C
    Hutchison, J
    McIntosh, MC
    ORGANIC LETTERS, 2005, 7 (17) : 3641 - 3644
  • [43] Ireland-Claisen rearrangements on chiral acids
    Doty, Amanda
    Campbell, Martin J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 801 - 801
  • [44] An Ireland-Claisen Rearrangement/Lactonisation Cascade as a Key Step in Studies Towards the Synthesis of (-)-Euonyminol
    Webber, Matthew J.
    Weston, Matthew
    Grainger, Damian M.
    Lloyd, Stacy
    Warren, Sarah A.
    Powell, Lyn
    Alanine, Alexander
    Stonehouse, Jeffrey P.
    Frampton, Christopher S.
    White, Andrew J. P.
    Spivey, Alan C.
    SYNLETT, 2011, (18) : 2693 - 2696
  • [45] Development of the Ireland-Claisen Rearrangement of Alkoxy- and Aryloxy-Substituted Allyl Glycinates
    Tellam, James P.
    Carbery, David R.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22): : 7809 - 7821
  • [46] Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids
    Fulton, Tyler J.
    Cusumano, Alexander Q.
    Alexy, Eric J.
    Du, Yun E.
    Zhang, Haiming
    Houk, K. N.
    Stoltz, Brian M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (52) : 21938 - 21947
  • [47] Ireland-Claisen Rearrangement of 6-Methylene-1,4-oxazepan-2-ones
    Smits, Gints
    Kinens, Artis
    Zemribo, Ronalds
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (30) : 6701 - 6709
  • [48] Application of chelation controlled Ireland-Claisen rearrangement in the total syntheses of Barmumycin and Limazepine E
    Smits, Gints
    Zemribo, Ronalds
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [49] 1,8-stereocontrol by 1,5-induction using an allylstannane followed by Ireland-Claisen rearrangement:: Diastereoselective total synthesis of (±)-patulolide C
    Dorling, EK
    Thomas, EJ
    TETRAHEDRON LETTERS, 1999, 40 (03) : 471 - 474
  • [50] Total Synthesis of the Putative Structure of Deoxypumiliotoxin 193H by an Ireland-Claisen Rearrangement
    Smits, Gints
    Zemribo, Ronalds
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (14) : 3152 - 3156
12345