Catalytic Enantio- and Diastereoselective Alkylations with Cyclic Sulfamidates

被引:36
|
作者
Moss, Thomas A. [2 ]
Alonso, Beatriz [1 ]
Fenwick, David R. [3 ]
Dixon, Darren J. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[3] Pfizer Global Res & Dev, Sandwich, Kent, England
基金
英国工程与自然科学研究理事会;
关键词
alkylation; contiguous stereocenters; phase-transfer catalysis; ring-opening reactions; sulfur heterocycles; PHASE-TRANSFER CATALYSIS; QUATERNARY AMMONIUM-SALTS; ALPHA-AMINO-ACIDS; BETA-KETO-ESTERS; ASYMMETRIC ALKYLATION; CONSTRUCTION; PRECURSORS; REACTIVITY; LACTAMS; STEREOCENTERS;
D O I
10.1002/anie.200905329
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Open for business: The enantio- and diastereoselective nucleophilic ring opening of five-membered and six-membered cyclic sulfamidates under asymmetric phase-transfer catalysis is presented. A range of pro-nucleophiles have been successfully alkylated in good yields and in good to excellent enantioselectivites. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:568 / 571
页数:4
相关论文
共 50 条
  • [21] Enantio- and diastereoselective synthesis of (R,R)-β-Methoxytyrosine
    Cranfill, David C.
    Lipton, Mark A.
    ORGANIC LETTERS, 2007, 9 (18) : 3511 - 3513
  • [22] Enantio- and Diastereoselective Synthesis of Spiro-epoxyoxindoles
    Boucherif, Amina
    Yang, Qing-Qing
    Wang, Qiang
    Chen, Jia-Rong
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 3924 - 3929
  • [23] Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst
    Kawauchi, Genki
    Umemiya, Shigenobu
    Taniguchi, Tohru
    Monde, Kenji
    Hayashi, Yujiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (33) : 8409 - 8414
  • [24] Enantio- and diastereoselective conjugate borylation/Mannich cyclization
    Larin, Egor M.
    Loup, Joachim
    Polishchuk, Iuliia
    Ross, Rachel J.
    Whyte, Andrew
    Lautens, Mark
    CHEMICAL SCIENCE, 2020, 11 (22) : 5716 - 5723
  • [25] An enantio- and diastereoselective approach to indoloquinolizidines in continuous flow
    Chaudhari, Moreshwar B.
    Gupta, Prachi
    Llanes, Patricia
    Zhou, Leijie
    Zanda, Nicola
    Pericas, Miquel A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (42) : 8273 - 8279
  • [26] Highly Enantio- and Diastereoselective Hydrogenation of Cyclic Tetra-Substituted β-Enamido Phosphorus Derivatives
    Zhang, Jun-Hao
    Xu, Hui
    Tang, Xiaodong
    Dang, Yanfeng
    Zhang, Fa-Guang
    Ma, Jun-An
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (28)
  • [27] Highly enantio- and diastereoselective catalytic one-pot synthesis of amino cyclopropyl carbinols
    Valenta, Petr
    Walsh, Patrick J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [28] ORGN 436-Catalytic enantio- and diastereoselective synthesis of allylic epoxides from propargylsilanes
    Aye, Yimon
    Evans, David A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [29] A General Strategy for the Catalytic, Highly Enantio- and Diastereoselective Synthesis of Indolizidine-Based Alkaloids
    Abels, Falko
    Lindemann, Chris
    Schneider, Christoph
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (07) : 1964 - 1979
  • [30] Cyclic nitriles: Diastereoselective alkylations
    Fleming, FF
    Gudipati, S
    Zhang, ZY
    Liu, W
    Steward, OW
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10): : 3845 - 3849