Indium-catalysed amide allylation of α-iminoamide: highly enantioselective synthesis of amide functionalised α-methylene-γ-butyrolactams

被引：7
作者：
Sengoku, Tetsuya [1 ]
Kokubo, Kana [1 ]
Sakamoto, Masami [2 ]
Takahashi, Masaki [1 ]
Yoda, Hidemi [1 ]
机构：
[1] Shizuoka Univ, Dept Appl Chem, Fac Engn, Naka Ku, 3-5-1 Johoku, Hamamatsu, Shizuoka 4328561, Japan
[2] Chiba Univ, Grad Sch Engn, Dept Appl Chem & Biotechnol, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 02期
关键词：
CARBONYL-COMPOUNDS; ASYMMETRIC ALLYLATION; IMINES; DERIVATIVES; ALDEHYDES; CONSTRUCTION; KETIMINES; ALLYLSTANNANES; NUCLEOPHILES; LACTONES;
D O I：
10.1039/c6ob02506d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective amide allylation of alpha-iminoamides has been achieved using catalytic amounts of InCl3, ZnCl2 and a BINOL derivative. This reaction allowed facile access to a variety of amide functionalised alpha-methylene-gamma-butyrolactams in excellent yields with high enantioselectivities.
引用
收藏
页码：320 / 323
页数：4
相关论文
共 35 条
[1]   Diastereoselective Construction of 3-Aminooxindoles with Adjacent Stereocenters: Stereocontrolled Addition of -Substituted Allylindiums to Isatin Ketimines [J].
Aslam, Nayyar Ahmad ;
Babu, Srinivasarao Arulananda ;
Rani, Soniya ;
Mahajan, Shivam ;
Solanki, Jagmohan ;
Yasuda, Makoto ;
Baba, Akio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (19) :4168-4189
[2]   SYNTHESIS OF POTENTIAL CYTOTOXIC ALPHA-METHYLENE GAMMA-LACTAMS [J].
BELAUD, C ;
ROUSSAKIS, C ;
LETOURNEUX, Y ;
ELALAMI, N ;
VILLIERAS, J .
SYNTHETIC COMMUNICATIONS, 1985, 15 (14) :1233-1243
[3]   Imidazolylpyridine-In(OTf)3 catalyzed enantioselective allylation of ketimines derived from isatins [J].
Chen, Tingting ;
Cai, Chun .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (22) :5019-5022
[4]   Asymmetric addition of allylic nucleophiles to imino compounds [J].
Ding, H ;
Friestad, GK .
SYNTHESIS-STUTTGART, 2005, (17) :2815-2829
[5]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[6]   Diastereoselective Indium-Promoted Allylation of Chiral N-Sulfinyl Imines [J].
Foubelo, Francisco ;
Yus, Miguel .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (03) :485-491
[7]  
Fu F., 2005, ORG LETT, V7, P2539
[8]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110
[9]   Catalytic asymmetric allylation of carbonyl compounds and imines with allylic boronates [J].
Huo, Hua-Xing ;
Duvall, Jeremy R. ;
Huang, Meng-Yuan ;
Hong, Ran .
ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (03) :303-320
[10]   Cu(I)-catalyzed asymmetric allylation of ketones and ketimines [J].
Kanai, Motomu ;
Wada, Reiko ;
Shibuguchi, Tomoyuki ;
Shibasaki, Masakatsu .
PURE AND APPLIED CHEMISTRY, 2008, 80 (05) :1055-1062
1234