Highly enantioselective Cr(salen)-catalyzed reaction of 2-(trimethylsilyloxy)furan and aldehydes. Effect of alcohol on enantioselectivity

被引:44
|
作者
Onitsuka, S
Matsuoka, Y
Irie, R
Katsuki, T [1 ]
机构
[1] Kyushu Univ 33, Fac Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan
[2] Japan Sci & Technol, CREST, JST, Higashi Ku, Fukuoka 8128581, Japan
关键词
D O I
10.1246/cl.2003.974
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reactions of 2-(trimethylsilyloxy)furan I and aldehydes catalyzed by a chiral cationic Cr(salen) complex proceeded with remarkably improved enantioselectivity, when a secondary alcohol was added. The role of the alcohol is acceleration of the conversion of an intermediary I-aldehyde adduct into the final product.
引用
收藏
页码:974 / 975
页数:2
相关论文
共 21 条
  • [1] Enantioselective addition of 2-(trimethylsilyloxy)furan to aldehydes using Cr(salen) as catalyst. Effect of water on enantioselectivity
    Matsuoka, Y
    Irie, R
    Katsuki, T
    CHEMISTRY LETTERS, 2003, 32 (07) : 584 - 585
  • [2] N-Heterocyclic Carbene Catalyzed Vinylogous Aldol Reaction of 2-(Trimethylsilyloxy) furan and Aldehydes
    Du, Guang-Fen
    He, Lin
    Gu, Cheng-Zhi
    Dai, Bin
    SYNLETT, 2010, (16) : 2513 - 2517
  • [3] Diastereoselective coupling reaction of moisture sensitive 2-(trimethylsilyloxy)furan with aldehydes in aqueous media
    Yu, CM
    Lee, J
    Lee, SS
    Choi, HS
    Park, SK
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1996, 17 (12) : 1104 - 1106
  • [4] Diastereoselective mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan catalyzed by bismuth triflate
    Ollevier, Thierry
    Bouchard, Jean-Emmanuel
    Desyroy, Valerie
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01): : 331 - 334
  • [5] Catalytic enantioselective Mukaiyama-Michael reaction of 2-(trimethylsilyloxy)furan with α′-phenylsulfonyl enones
    Yang, Hyeyeon
    Kim, Sunggak
    SYNLETT, 2008, (04) : 555 - 560
  • [6] Highly diastereoselective vinylogous Mukaiyama aldol reaction of α-keto phosphonates with 2-(trimethylsilyloxy)furan catalyzed by Cu(OTf)2
    Yu, Jipan
    Zhao, Xiaona
    Miao, Zhiwei
    Chen, Ruyu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6721 - 6726
  • [7] Highly enantioselective addition of Me2Zn to aldehydes catalyzed by ClCr(Salen)
    Cozzi, PG
    Kotrusz, P
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) : 4940 - 4941
  • [8] Highly enantioselective addition of Me2Zn to aldehydes catalyzed by ClCr(Salen)
    Cozzi, Pier Giorgio
    Kotrusz, Peter
    Journal of the American Chemical Society, 2006, 128 (15): : 4940 - 4941
  • [9] Highly enantioselective Cr(salen)-catalyzed Mukaiyama Aldol reaction:: Construction of δ-hydroxy-β-keto ester derivatives
    Shimada, Y
    Matsuoka, Y
    Irie, R
    Katsuki, T
    SYNLETT, 2004, (01) : 57 - 60
  • [10] HIGHLY DIASTEREOSELECTIVE VINYLOGOUS MUKAIYAMA ALDOL REACTION OF ISATINS WITH 2-(TRIMETHYLSILYLOXY) FURANS CATALYZED BY QUININE
    Kong, Shasha
    Fan, Weidong
    Lyu, Hairong
    Zhan, Junchen
    Miao, Xinyu
    Miao, Zhiwei
    SYNTHETIC COMMUNICATIONS, 2014, 44 (07) : 936 - 942