Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl3

被引:8
|
作者
Lopez-Martinez, Josefa L. [1 ]
Torres-Garcia, Irene [1 ]
Rodriguez-Garcia, Ignacio [1 ]
Munoz-Dorado, Manuel [1 ]
Alvarez-Corral, Miriam [1 ]
机构
[1] Univ Almeria, Dept Quim Organ, CeiA3, Almeria 04120, Spain
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 02期
关键词
ASYMMETRIC ALLYLATION; ALDEHYDES; COMPLEXES;
D O I
10.1021/acs.joc.8b02643
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N center dot HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis of natural products.
引用
收藏
页码:806 / 816
页数:11
相关论文
共 50 条
  • [21] Diastereoselective Barbier-type and palladium-mediated allylation of optically active aldimine with allylindium reagents
    Yanada, R
    Kaieda, A
    Takemoto, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22): : 7516 - 7518
  • [22] Indium-promoted barbier-type allylations in aqueous media:: New access to 2-C- and 4-C-branched sugars
    Lubineau, A
    Canac, Y
    Le Goff, N
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (3-4) : 319 - 327
  • [23] Asymmetric indium-mediated Barbier-type allylation reactions with ketones to form homoallylic alcohol products
    Haddad, Terra D.
    Hirayama, Lacie C.
    Taynton, Philip
    Singaram, Bakthan
    TETRAHEDRON LETTERS, 2008, 49 (03) : 508 - 511
  • [24] Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions
    Vogel, S
    Stembera, K
    Hennig, L
    Findeisen, M
    Giesa, S
    Welzel, P
    Lampilas, M
    TETRAHEDRON, 2001, 57 (19) : 4139 - 4146
  • [25] A convenient procedure for bismuth-mediated Barbier-type allylation of aldehydes in water containing fluoride ions
    Smith, K
    Lock, S
    El-Hiti, GA
    Wada, M
    Miyoshi, N
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (06) : 935 - 938
  • [26] Superior Alkylating Agents for Bulky Esters/Ketones via Strontium-Mediated Barbier-Type Reaction
    Ohmura, Satoshi D.
    Miyazaki, Yasuaki
    Kanehiro, Daisuke
    Yamaguchi, Yuka
    Kitakata, Saki
    Tateda, Sawa
    Nishizawa, Takahiro
    Shimoda, Ryosuke
    Nagaoka, Gen
    Ueno, Masaharu
    Miyoshi, Norikazu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 821 - 824
  • [27] A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions
    Yin, JieXiang
    Stark, Roderick T.
    Fallis, Ian A.
    Browne, Duncan L.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (04): : 2347 - 2354
  • [28] A synthesis of 3-substituted 3-hydroxyoxindoles via an indium-mediated Barbier-type allylation of isatins in PEG-400
    Chen, Junmin
    Yuan, Tangjun
    Liu, Li
    JOURNAL OF CHEMICAL RESEARCH, 2011, (07) : 390 - 393
  • [29] Indium-promoted Barbier-type allylations in aqueous media:: a convenient approach to 4-C-branched monosaccharides and (1→4)-C-disaccharides
    Levoirier, E
    Canac, Y
    Norsikian, S
    Lubineau, A
    CARBOHYDRATE RESEARCH, 2004, 339 (17) : 2737 - 2747
  • [30] CONSTRUCTION OF ALL-CARBON QUATERNARY STEREOCENTERS BY ZINC-MEDIATED BARBIER-TYPE ALLYLATION IN AQUEOUS MEDIA
    Takao, Ken-ichi
    Miyashita, Tomo
    Akiyama, Nozomi
    Kurisu, Takuya
    Tsunoda, Kohei
    Tadano, Kin-ichi
    HETEROCYCLES, 2012, 86 (01) : 147 - 153