Zinc Radical Transfer Based Modular Approach to Enantiopure Alkylidene‐β‐prolines from N‐(tert‐Butylsulfinyl)‐α‐(aminomethyl)acrylates
作者： Redouane Beniazza , Elise Romain , Fabrice Chemla , Franck Ferreira , Olivier Jackowski
关键词:
摘要: N-(tert-Butylsulfinyl)-α-(aminomethyl)acrylates with tethered silylated alkynes undergo a tandem 1,4-addition/carbozincation reaction upon exposure to dialkylzinc compounds in the presence of air. The process follows zinc-radical-transfer mechanism and provides vinylzinc adducts that can react subsequently electrophiles. High levels chiral induction (dr > 90:10) from tert-butylsulfinyl directing group are achieved during radical 5-exo-dig cyclization by adding samarium(III) triflate. sequence overall straightforward modular access enantiopure (E)-4-alkylidene-β-prolines tert-butanesulfinamide.
sci-hub.se 参考文章(33)
José A. Fernández-Salas, M. Mercedes Rodríguez-Fernández, M. Carmen Maestro, José L. García-Ruano, Synthesis of Enantiomerically Pure (α‐Phenylalkyl)amines with Substituents at the ortho Position through Diastereoselective Radical Alkylation Reaction of Sulfinimines European Journal of Organic Chemistry. ,vol. 2014, pp. 5265- 5272 ,(2014) , 10.1002/EJOC.201402355
Akio Kamimura, Shingo Ishikawa, Fumiaki Noguchi, Takaaki Moriyama, Masahiro So, Toshihiro Murafuji, Hidemitsu Uno, Unexpected formation of stannolanes and trigonal bipyramidal tin complexes by radical cyclization reaction. Chemical Communications. ,vol. 48, pp. 6592- 6594 ,(2012) , 10.1039/C2CC31753B
José A. Fernández-Salas, M. Mercedes Rodríguez-Fernández, M. Carmen Maestro, José L. García-Ruano, Stereochemical aspects and the synthetic scope of the SHi at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides Chemical Communications. ,vol. 50, pp. 6046- 6048 ,(2014) , 10.1039/C4CC01831A
Zili Chen, Yu-Xin Zhang, Yan An, Xin-Li Song, Ya-Hui Wang, Li-Li Zhu, Lin Guo, Radical Addition of Ethers to Terminal Alkynes with High E‐Selectivity European Journal of Organic Chemistry. ,vol. 2009, pp. 5146- 5152 ,(2009) , 10.1002/EJOC.200900858
Tony P. Tang, Jonathan A. Ellman, The tert-Butanesulfinyl Group: An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of beta-Amino Acids. Journal of Organic Chemistry. ,vol. 64, pp. 12- 13 ,(1999) , 10.1021/JO9820824
Fabrice Chemla, Florian Dulong, Franck Ferreira, Alejandro Pérez-Luna, Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs. Beilstein Journal of Organic Chemistry. ,vol. 9, pp. 236- 245 ,(2013) , 10.3762/BJOC.9.28
Janusz Lewiński, Witold Śliwiński, Maciej Dranka, Iwona Justyniak, Janusz Lipkowski, Reactions of [ZnR2(L)] complexes with dioxygen: a new look at an old problem. Angewandte Chemie. ,vol. 45, pp. 4826- 4829 ,(2006) , 10.1002/ANIE.200601001
Gaëlle Fourrière, Nathalie Van Hijfte, Jérôme Lalot, Guy Dutech, Bruno Fragnet, Gaël Coadou, Jean-Charles Quirion, Eric Leclerc, Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides Tetrahedron. ,vol. 66, pp. 3963- 3972 ,(2010) , 10.1016/J.TET.2010.03.079
Yu-Wu Zhong, Yi-Zhou Dong, Kai Fang, Kenji Izumi, Ming-Hua Xu, Guo-Qiang Lin, A Highly Efficient and Direct Approach for Synthesis of Enantiopure β-Amino Alcohols by Reductive Cross-Coupling of ChiralN-tert-Butanesulfinyl Imines with Aldehydes Journal of the American Chemical Society. ,vol. 127, pp. 11956- 11957 ,(2005) , 10.1021/JA054401W
Elisabetta Mileo, Fides Benfatti, Pier Giorgio Cozzi, Marco Lucarini, Me2Zn as a radical source in Reformatsky-type reactions Chemical Communications. pp. 469- 470 ,(2009) , 10.1039/B818437B