Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines

被引：336
|
作者：
Cogan, DA [1 ]
Liu, GC [1 ]
Ellman, J [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 29期
关键词：
amines; asymmetric reactions; diastereoselection; imines; sulfinamides;
D O I：
10.1016/S0040-4020(99)00451-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
High yielding and highly diastereoselective methods for I,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert-butanesulfinyl ketimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6) delivers highly enantioenriched alpha-branched and alpha,alpha-dibranched amines. Since a broad range of sulfinyl imines are easily accessible from aldehydes and ketones, a wide variety of enantioentriched amines may be prepared. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8883 / 8904
页数：22
相关论文
共 50 条
  • [21] Highly stereoselective addition of organometallic reagents to N-tert-butanesulfinyl imines derived from 3-and 4-substituted cyclohexanones
    McMahon, JP
    Ellman, JA
    ORGANIC LETTERS, 2004, 6 (10) : 1645 - 1647
  • [22] Diastereoselective Homoallylation and Bis-homoallylation of N-tert-butanesulfinyl Imines with Organomagnesium Compounds
    Sirvent, Ana
    Foubelo, Francisco
    LETTERS IN ORGANIC CHEMISTRY, 2018, 15 (05) : 345 - 348
  • [23] Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides
    Xue, Zheng
    Dee, Veronica M.
    Hope-Weeks, Louisa J.
    Whittlesey, Bruce R.
    Mayer, Michael F.
    ARKIVOC, 2010, : 65 - 80
  • [24] A Highly Stereoselective Addition of Lithiated Ynamides to Ellman-Davis Chiral N-tert-Butanesulfinyl Imines
    Wang, Xiao-Na
    Hsung, Richard P.
    Qi, Rui
    Fox, Sierra K.
    Lv, Ming-Can
    ORGANIC LETTERS, 2013, 15 (10) : 2514 - 2517
  • [25] Chiral N-tert-butanesulfinyl α,β-unsaturated ketimine: a simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions
    Feng, Xiangqing
    Wei, Beibei
    Yang, Jing
    Du, Haifeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (17) : 5927 - 5929
  • [26] Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines
    Xiao, Hengqiao
    Huang, Yangen
    Qing, Feng-Ling
    TETRAHEDRON-ASYMMETRY, 2010, 21 (24) : 2949 - 2955
  • [27] Indium-mediated diastereoselective allylation of N-tert-butanesulfinyl imines derived from α-ketoesters
    Macia, Edgar
    Foubelo, Francisco
    Yus, Miguel
    TETRAHEDRON, 2016, 72 (40) : 6001 - 6010
  • [28] Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facile and Rapid Access to (-)-Cytoxazone
    Liu, Min
    Sun, Xing-Wen
    Xu, Ming-Hua
    Lin, Guo-Qiang
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) : 10217 - 10224
  • [29] Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
    Almansa, Raquel
    Collados, Juan F.
    Guijarro, David
    Yus, Miguel
    TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1421 - 1431
  • [30] Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: dual stereocontrol with nearly perfect diastereoselectivity
    Zhao, Yi-Shuang
    Liu, Qiang
    Tian, Ping
    Tao, Jing-Chao
    Lin, Guo-Qiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) : 4174 - 4178
12345