Palladium-Catalyzed Asymmetric Synthesis of 2-Alkynyl Oxacycles

被引：27
作者：
Daniels, David S. B. [1 ]
Thompson, Amber L. [1 ]
Anderson, Edward A. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Oxford OX1 3TA, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 48期
基金：
英国工程与自然科学研究理事会;
关键词：
alkynes; asymmetric synthesis; cyclization; oxygen heterocycles; palladium; ALKYNYL CYCLIC CARBONATES; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION; HETEROCYCLES; ALCOHOLS; ALLENES;
D O I：
10.1002/anie.201105720
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Oxyacetylene: Unusual palladium-catalyzed cyclizations of cyclic and acyclic propargylic carbonates give 2-alkynyl oxacycles. The reactions proceed with very high stereoselectivity for both syn- and anti-disubstituted furans and pyrans, and with exceptional regioselectivity. In addition, two-directional cyclizations of bis-propargylic carbonate substrates yield bifurans with complete stereocontrol for all diastereomers. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：11506 / 11510
页数：5
相关论文
共 58 条
  • [1] SIR92 - a program for automatic solution of crystal structures by direct methods
    ALTOMARE, A
    CASCARANO, G
    GIACOVAZZO, G
    GUAGLIARDI, A
    BURLA, MC
    POLIDORI, G
    CAMALLI, M
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 : 435 - 435
  • [2] [Anonymous], 2009, ANGEW CHEM
  • [3] [Anonymous], 2003, ANGEW CHEM
  • [4] Chirality Transfer in Au-Catalyzed Cyclization Reactions of Monoallylic Diols: Selective Access to Specific Enantiomers Based on Olefin Geometry
    Aponick, Aaron
    Biannic, Berenger
    [J]. ORGANIC LETTERS, 2011, 13 (06) : 1330 - 1333
  • [5] Acetogenins from Annonaceae:: recent progress in isolation, synthesis and mechanisms of action
    Bermejo, A
    Figadère, B
    Zafra-Polo, MC
    Barrachina, I
    Estornell, E
    Cortes, D
    [J]. NATURAL PRODUCT REPORTS, 2005, 22 (02) : 269 - 303
  • [6] CRYSTALS version 12: software for guided crystal structure analysis
    Betteridge, PW
    Carruthers, JR
    Cooper, RI
    Prout, K
    Watkin, DJ
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2003, 36 : 1487 - 1487
  • [7] Boyer A., 2009, ANGEW CHEM, V121, P1343
  • [8] Second-Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment
    Boyer, Alistair
    Veitch, Gemma E.
    Beckmann, Edith
    Ley, Steven V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (07) : 1317 - 1320
  • [9] Brabander J. K. D, 2008, ORG LETT, V10, P2533
  • [10] BURTON JW, 2009, ORG BIOMOL CHEM, V7, P238
123456