Stereoselective synthesis of α-(dichloromethyl)amines, α-(chloromethyl)amines, and α-chloroaziridines

被引：17
|
作者：
Li, Desheng [1 ]
Li, Ya [1 ]
Chen, Zhiqiu [1 ]
Shang, Huaqi [1 ]
Li, Hongsen [1 ]
Ren, Xinfeng [1 ]
机构：
[1] Shanghai Univ Engn Sci, Dept Chem & Chem Engn, Shanghai 201620, Peoples R China
来源：
RSC ADVANCES | 2014年 / 4卷 / 27期
基金：
中国国家自然科学基金;
关键词：
HALOGENATED IMINO COMPOUNDS; CHIRAL N-ACYLHYDRAZONES; ASYMMETRIC-SYNTHESIS; RADICAL-ADDITION; FACILE SYNTHESIS; FUNCTIONALIZED AZIRIDINES; STEREOSPECIFIC SYNTHESIS; ACID-CHLORIDES; REDUCTION; REARRANGEMENT;
D O I：
10.1039/c4ra00471j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Protocols for the stereoselective synthesis of alpha-(dichloromethyl)amines, alpha-(chloromethyl)amines, and alpha-chloroaziridines are presented. Diastereoselective synthesis of alpha-(dichloromethyl)amines was achieved based on nucleophilic dichloromethylation of aromatic N-tert-butylsulfinyl aldimines with (dichloromethyl)trimethylsilane at a low reaction temperature. Slowly warming the reaction mixture up to room temperature gave alpha-chloro cis-aziridines. Additionally, with Bu3SnH as the reductant, alpha-(dichloromethyl)amines were readily obtained from easily accessible alpha-(trichloromethyl)amines via mono-dechlorination. Over-reduction was successfully suppressed. Subsequent radical mono-dechlorination of the alpha-(dichloromethyl)amines gave the corresponding alpha-(chloromethyl)amines in good to excellent yields.
引用
收藏
页码：14254 / 14263
页数：10
相关论文
共 50 条
  • [1] Stereoselective Synthesis of Alicylic Amines
    Kristoffer F. Graham
    Kenneth T. Hindle
    S. David Jackson
    David J. M. Williams
    Stefan Wuttke
    Topics in Catalysis, 2010, 53 : 1121 - 1125
  • [2] Stereoselective Synthesis of Alicylic Amines
    Graham, Kristoffer F.
    Hindle, Kenneth T.
    Jackson, S. David
    Williams, David J. M.
    Wuttke, Stefan
    TOPICS IN CATALYSIS, 2010, 53 (15-18) : 1121 - 1125
  • [3] A GENERAL, HIGHLY STEREOSELECTIVE SYNTHESIS OF AMINES
    WROBEL, JE
    GANEM, B
    TETRAHEDRON LETTERS, 1981, 22 (36) : 3447 - 3450
  • [4] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF STEROIDAL AMINES
    KOGA, T
    NOGAMI, Y
    YAMANAKA, S
    SYNTHESIS-STUTTGART, 1986, (06): : 461 - 464
  • [5] A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF ALLYLIC AND HOMOALLYLIC AMINES
    DESHONG, P
    LEGINUS, JM
    LANDER, SW
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04): : 574 - 576
  • [6] REACTION OF CHLOROMETHYL ETHER WITH PRIMARY AMINES
    ULRICH, H
    RUBINFEL.J
    JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05): : 1637 - &
  • [7] Stereoselective Synthesis of Tertiary Allylic Amines by Titanium-Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines
    Kaper, Tobias
    Geik, Dennis
    Fornfeist, Felix
    Schmidtmann, Marc
    Doye, Sven
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (10)
  • [8] PREPARATION AND INVESTIGATION OF DICHLOROMETHYL-SUBSTITUTED AMINES AND FORMAMIDINES
    ALLENSTEIN, E
    SILLE, F
    CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (03): : 921 - 931
  • [9] PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF ALLYLIC AMINES
    TAMARU, Y
    BANDO, T
    KAWAMURA, Y
    OKAMURA, K
    YOSHIDA, Z
    SHIRO, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (20) : 1498 - 1500
  • [10] α-Aminoallylation of aldehydes with ammonia:: Stereoselective synthesis of homoallylic primary amines
    Sugiura, M
    Hirano, K
    Kobayashi, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (23) : 7182 - 7183
12345