A Lewis Acid Promoted Oxidative Cyclization

被引:22
|
作者
Donohoe, Timothy J. [1 ]
Winship, Paul C. M.
Walter, Daryl S.
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
来源
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 16期
关键词
OSMIUM;
D O I
10.1021/jo901243y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Replacing trifluoroacetic acid with it catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little its 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.
引用
收藏
页码:6394 / 6397
页数:4
相关论文
共 50 条
  • [31] A SELECTIVE SYNTHESIS OF 3-ALKYL-4-HALOTETRAHYDROPYRANS VIA THE LEWIS ACID PROMOTED CYCLIZATION OF UNSATURATED ACETALS
    THOMPSON, DW
    WINSTEAD, RC
    SIMPSON, TH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 146 - ORN
  • [32] HIGHLY STEREOSELECTIVE CYCLIZATION OF EPOXYKETONE PROMOTED BY ACID
    SUZUKI, T
    SATO, E
    IHARA, H
    UNNO, K
    KAMETANI, T
    HETEROCYCLES, 1988, 27 (01) : 21 - 24
  • [33] LEWIS ACID MEDIATED CYCLIZATION OF EPOXY BENZOYLCARBAMATES
    YAMAMOTO, M
    SUZUKI, M
    KISHIKAWA, K
    KOHMOTO, S
    SYNTHESIS-STUTTGART, 1993, (03): : 307 - 310
  • [34] LEWIS-ACID CATALYZED CYCLIZATION OF GERANYLACETONE
    SCHULTEELTE, KH
    OHLOFF, G
    HELVETICA CHIMICA ACTA, 1975, 58 (01) : 18 - 27
  • [35] IODINE PROMOTED THERMAL CYCLIZATION OF ANTHRANILIC ACID
    BHATTACHARYYA, P
    SARKAR, M
    BISWAS, AK
    CHAKRABORTY, DP
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1979, 56 (03) : 328 - 329
  • [36] Lewis acid promoted direct synthesis of tetraalkynylstannanes
    Levashov, A. S.
    Andreev, A. A.
    Konshin, V. V.
    TETRAHEDRON LETTERS, 2015, 56 (14) : 1870 - 1872
  • [37] Lewis Acid Promoted Vicinal Oxytrifluoromethylselenolation of Alkenes
    Li, Yang
    Zhang, Shangbiao
    Wang, Yanan
    Gao, Yan
    Chen, Chao
    Yuan, Zheliang
    ORGANIC LETTERS, 2023, 25 (18) : 3210 - 3215
  • [38] Addition of diethylzine to imines promoted by Lewis acid
    Hou, XL
    Zheng, XL
    Dai, LX
    TETRAHEDRON LETTERS, 1998, 39 (38) : 6949 - 6952
  • [39] A Lewis acid-promoted Pinner reaction
    Pfaff, Dominik
    Nemecek, Gregor
    Podlech, Joachim
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1572 - 1577
  • [40] Gold vs. hard Lewis acids: Propargyl ester rearrangement promoted cyclization vs. cyclization promoted propargyl ester rearrangement
    Cran, John W.
    Vidhani, Dinesh V.
    Krafft, Marie E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245