BF3•OEt2/TMSN3 Mediated Regioselective Azidolysis of Vinylaziridines

被引：7
|
作者：
Righi, Giuliana [1 ]
Bovicelli, Paolo [2 ]
Marucci, Cristina [3 ]
Tirotta, Ilarai [3 ]
机构：
[1] CNR ICB, Unity Rome, I-00185 Rome, Italy
[2] CNR ICB, Unity Sassari, I-07040 Sassari, Italy
[3] Univ Roma La Sapienza, Dept Chem, I-00185 Rome, Italy
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 20期
关键词：
vinylepoxides; vinylaziridines; azidolysis; azido alcohols; azido amines; WADSWORTH-EMMONS OLEFINATION; ESTERS;
D O I：
10.1055/s-0032-1316768
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An easy and general azidolysis of vinylepoxides mediated by BF3 center dot OEt2 and TMSN3 recently reported by our group has been extended to vinylaziridines. The reaction affords unsaturated azido derivatives with complete stereoselectivity and regioselectivity, when in the presence of electron-poor olefins, regardless of the size of substituents on the heterocyclic ring.
引用
收藏
页码：3202 / 3208
页数：7
相关论文
共 50 条
  • [41] New olefination of acetals with TMSCH2Cu(PBu3)•LiI under the influence of BF3•OEt2
    Suzuki, T
    Oriyama, T
    SYNLETT, 2000, (06) : 859 - 861
  • [42] An expeditious method to synthesize difluoroboron complexes of β-keto amides from β-keto nitriles and BF3•OEt2
    Xu, Chuangchuang
    Xu, Jiaxi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (30) : 6375 - 6383
  • [43] XPS研究BF3·OEt2对HZSM—5沸石的脱铝作用
    金亚明
    南京师大学报(自然科学版), 1992, (03) : 52 - 56
  • [44] Nucleophilic Addition of Potassium Alkynyltrifluoroborates to D-Glucal Mediated by BF3•OEt2: Highly Stereoselective Synthesis of α-C-glycosides
    Vieira, Adriano S.
    Fiorante, Pedro F.
    Hough, Thomas L. S.
    Ferreira, Fernando P.
    Ludtke, Diogo S.
    Stefani, Helio A.
    ORGANIC LETTERS, 2008, 10 (22) : 5215 - 5218
  • [45] A rapid and highly efficient Michael addition of methoxybenzenes and indoles to α,β-unsaturated ketones using BF3•OEt2 as a catalyst
    Swetha, A.
    Reddy, M. Raghavender
    Babu, B. Madhu
    Meshram, H. M.
    TETRAHEDRON LETTERS, 2017, 58 (47) : 4427 - 4431
  • [46] BF3•OEt2 enhanced Yb(OTf)3-promoted glycosidation of 1-O-acyl-D-glucopyranose
    Yamanoi, T
    Iwai, Y
    Inazu, T
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (4-5) : 819 - 822
  • [47] Reduction of quinolines to 1,2,3,4-tetrahydro derivatives employing a combination of NaCNBH3 and BF3 QQ OEt2
    Srikrisha, A.
    Jagadeeswar Reddy, T.
    Viswajanani, R.
    Tetrahedron, 52 (05):
  • [48] BF3·OEt2在镍体系催化丁二烯聚合中的作用
    陈滇宝
    王春
    仲崇祺
    唐学明
    应用化学, 1988, (06) : 19 - 23
  • [49] Revisit of the phenol O-glycosylation with glycosyl imidates, BF3•OEt2 is a better catalyst than TMSOTf
    Li, Yali
    Mo, Huaping
    Lian, Gaoyan
    Yu, Biao
    CARBOHYDRATE RESEARCH, 2012, 363 : 14 - 22
  • [50] BF3•OEt2 in Alcoholic Media, an Efficient Initiator in the Cationic Polymerization of Phenyl-1,3-benzoxazines
    Andreu, Robert
    Galia, Marina
    Cadiz, Virginia
    Lligadas, Gerard
    Reina, Jose A.
    Ronda, Juan C.
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (23) : 5075 - 5084
12345