Z-Selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocyclic alkenes

被引:11
|
作者
Ando, Kaori [1 ]
Sato, Kaori [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan
关键词
Z-UNSATURATED ESTERS; ETHYL (DIARYLPHOSPHONO)ACETATES; ANISOMELIC ACID; OLEFINATION; ALDEHYDES; STEREOCHEMISTRY; CYCLIZATION; EFFICIENT; REAGENTS; BASE;
D O I
10.1016/j.tetlet.2011.01.043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)(2)P(O)CHR'CO(2)Et (R' = (CH(2))(n)CHO) (R = Ph or o-tBuC(6)H(4)) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1284 / 1287
页数:4
相关论文
共 50 条
  • [41] DIFFERENTIATION OF ENANTIOTOPIC CARBONYL GROUPS BY THE HORNER-WADSWORTH-EMMONS REACTION
    TANAKA, K
    OHTA, Y
    FUJI, K
    TAGA, T
    TETRAHEDRON LETTERS, 1993, 34 (25) : 4071 - 4074
  • [42] An improved synthesis of the (E,Z)-dienoate precursor of (+)-damavaricin D via a vinylogous Horner-Wadsworth-Emmons reaction
    Chemler, SR
    Coffey, DS
    Roush, WR
    TETRAHEDRON LETTERS, 1999, 40 (07) : 1269 - 1272
  • [43] The Horner-Wadsworth-Emmons reaction in the synthesis of macrocyclic peptides: the Trp-His-Gly-Arg derived macrocycle of moroidin
    Harrison, JR
    Moody, CJ
    TETRAHEDRON LETTERS, 2003, 44 (28) : 5189 - 5191
  • [44] Horner-Wadsworth-Emmons olefination of proteins and glycoproteins
    Angelastro, Antonio
    Barkhanskiy, Alexey
    Journeaux, Toby
    Sivapalan, Rohan
    King, Thomas A.
    Perez, Laura Rodriguez
    Goundry, William R. F.
    Barran, Perdita
    Flitsch, Sabine L.
    NATURE SYNTHESIS, 2024, 3 (08): : 976 - 985
  • [45] Solvent-free Horner-Wadsworth-Emmons reaction using DBU
    Ando, Kaori
    Yamada, Kyohei
    TETRAHEDRON LETTERS, 2010, 51 (25) : 3297 - 3299
  • [46] Enantioselective Horner-Wadsworth-Emmons reaction for the asymmetric synthesis of α-fluoro-α,β-unsaturated esters
    Sano, S
    Yokoyama, K
    Teranishi, R
    Shiro, M
    Nagao, Y
    TETRAHEDRON LETTERS, 2002, 43 (02) : 281 - 284
  • [47] Practical synthesis of DQ-113, a new quinolone antibacterial agent, by using the intramolecular Horner-Wadsworth-Emmons reaction
    Inagaki, H
    Takeda, T
    Miyauchi, RN
    Kawakami, K
    Takahashi, H
    Takemura, M
    HETEROCYCLES, 2004, 63 (03) : 699 - 706
  • [48] Z-Selective Horner-Wadsworth-Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[Z)-CF=C1-Pro-OH dipeptide isostere
    Sano, Shigeki
    Matsumoto, Tomoya
    Nanataki, Hiroshi
    Tempaku, Shota
    Nakao, Michiyasu
    TETRAHEDRON LETTERS, 2014, 55 (45) : 6248 - 6251
  • [49] The Asymmetric Horner-Wadsworth-Emmons Reaction Mediated by an External Chiral Ligand
    Grad. Sch. of Pharmaceutical Sci., Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-01, Japan
    Angew. Chem. Int. Ed., 4 (515-517):
  • [50] N-Alkylation of α-Iminophosphonates and Application to Horner-Wadsworth-Emmons Reaction
    Shimizu, Makoto
    Tateishi, Masasato
    Mizota, Isao
    CHEMISTRY LETTERS, 2014, 43 (11) : 1752 - 1754