Stereoselective TiCl4-Mediated Aldol Reactions Starting from Acylsilanes

被引:4
|
作者
Marri, Gangababu [1 ]
Reddy, J. Satyanarayana [1 ]
Ruiz, Johal [2 ]
Das, Saibal [1 ]
Gree, Rene [2 ]
机构
[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
[2] Univ Rennes 1, Inst Sci Chim Rennes, CNRS, UMR 6226, F-35042 Rennes, France
关键词
Silanes; Aldol reactions; Silicon; Lewis acids; ADDITIONS; REAGENTS; ASSEMBLAGE; MECHANISM; ALDEHYDES; ACETATES; SYN;
D O I
10.1002/ejoc.201403263
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient method for the preparation of beta-hydroxyacylsilanes has been developed through a TiCl4-mediated aldol reaction. A selection of Lewis acids has been assessed, and other parameters such as solvent and temperature have been optimized. These aldol reactions occur under mild conditions and furnish a selection of beta-hydroxy acylsilanes in fair-to-good yields with high syn selectivities (up to 99%).
引用
收藏
页码:840 / 846
页数:7
相关论文
共 50 条
  • [1] Highly stereoselective TiCl4-mediated aldol reactions from (S)-2-benzyloxy-3-pentanone
    Rodriguez-Cisterna, Victor
    Villar, Cristina
    Romea, Pedro
    Urpi, Felix
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17): : 6631 - 6633
  • [2] Rate enhancement by water in a TiCl4-mediated stereoselective vinylogous Mukaiyama aldol reaction
    Yamaoka, Makoto
    Nakazaki, Atsuo
    Kobayashi, Susumu
    TETRAHEDRON LETTERS, 2010, 51 (02) : 287 - 289
  • [3] DIASTEREOSELECTIVITY IN THE TICL4-MEDIATED ALDOL REACTION OF CYCLIC DIENYLSILYL ETHERS
    BARNER, BA
    LIU, YL
    RAHMAN, MA
    TETRAHEDRON, 1989, 45 (19) : 6101 - 6112
  • [4] TiCl4-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base
    Li, GG
    Wei, HX
    Gao, JJ
    Caputo, TD
    TETRAHEDRON LETTERS, 2000, 41 (01) : 1 - 5
  • [5] Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction
    Liu, He
    Yang, Wenjiao
    Zheng, Shaojiu
    He, Yang
    Wang, Guan
    Qin, Hongjian
    Zhu, Fuqiang
    Jiang, Xiangrui
    Shen, Jingshan
    Gong, Xudong
    TETRAHEDRON LETTERS, 2022, 95
  • [6] TICL4-MEDIATED REACTIONS OF ALKYL AZIDES WITH CYCLIC-KETONES
    AUBE, J
    MILLIGAN, GL
    MOSSMAN, CJ
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06): : 1635 - 1637
  • [7] STEREOSELECTIVE ALDOL REACTIONS USING TICL4 AS STEREOCHEMICAL TEMPLATE
    GENNARI, C
    BERNARDI, A
    SCOLASTICO, C
    POTENZA, D
    TETRAHEDRON LETTERS, 1985, 26 (34) : 4129 - 4132
  • [8] TiCl4-mediated amination of propargylic esters
    Mahrwald, R
    Quint, S
    TETRAHEDRON LETTERS, 2001, 42 (09) : 1655 - 1656
  • [9] On the mechanism of directed, TiCl4-mediated aldol addition -: an easy access to substituted 2.4-furandiols
    Mahrwald, R
    Ziemer, B
    Troyanov, S
    TETRAHEDRON LETTERS, 2001, 42 (39) : 6843 - 6845
  • [10] TiCl4-mediated nucleophilic substitution of propargylic esters
    Mahrwald, R
    Quint, S
    TETRAHEDRON, 2000, 56 (38) : 7463 - 7468