Synthesis of Enantiomerically Pure (α‐Phenylalkyl)amines with Substituents at the ortho Position through Diastereoselective Radical Alkylation Reaction of Sulfinimines
作者： José A. Fernández-Salas , M. Mercedes Rodríguez-Fernández , M. Carmen Maestro , José L. García-Ruano
关键词:
摘要: The alkyl radical (R1) addition reaction to ortho-X-substituted N-(benzylidene)-2-methylpropane-2-sulfinamides (X = Br, CN, CO2Me, OH and OMe) is highly diastereoselective, regardless of the electronic properties X group size R1. Easy removal sulfinyl provides title compounds in enantiomerically pure form. This two-step sequence has been successfully applied preparation primary α-(tert-butyl)-ortho-hydroxy- -ortho-methoxybenzylamines, as well 3-isopropyl-substituted isoindolin-1-one.
sci-hub.se 参考文章(64)
John B. Brazier, Nicholas C. O. Tomkinson, Secondary and Primary Amine Catalysts for Iminium Catalysis Topics in Current Chemistry. ,vol. 291, pp. 281- 347 ,(2010) , 10.1007/978-3-642-02815-1_28
Olga Lifchits, Manuel Mahlau, Corinna M. Reisinger, Anna Lee, Christophe Farès, Iakov Polyak, Gopinadhanpillai Gopakumar, Walter Thiel, Benjamin List, The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide. Journal of the American Chemical Society. ,vol. 135, pp. 6677- 6693 ,(2013) , 10.1021/JA402058V
Dipshikha Banerjee, Andrea K. Buzas, Céline Besnard, E. Peter Kündig, Chiral N-Heterocyclic Carbene Gold Complexes: Synthesis, Properties, and Application in Asymmetric Catalysis Organometallics. ,vol. 31, pp. 8348- 8354 ,(2012) , 10.1021/OM300917M
Derek A. Cogan, Guangcheng Liu, Jonathan Ellman, Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines Tetrahedron. ,vol. 55, pp. 8883- 8904 ,(1999) , 10.1016/S0040-4020(99)00451-2
Takeaki Naito, Development of new synthetic reactions for nitrogen-containing compounds and their application. Chemical & Pharmaceutical Bulletin. ,vol. 56, pp. 1367- 1383 ,(2008) , 10.1248/CPB.56.1367
Maria Laura Bolognesi, Manuela Bartolini, Michela Rosini, Vincenza Andrisano, Carlo Melchiorre, Structure-activity relationships of memoquin: Influence of the chain chirality in the multi-target mechanism of action. Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 4312- 4315 ,(2009) , 10.1016/J.BMCL.2009.05.087
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
Dongeun Kim, Lucia Lozano, Suk Bin Kong, Hyunsoo Han, Jae Seung Lee, Concise asymmetric synthesis of orthogonally protected syn- and anti-1,3-aminoalcohols. Organic Letters. ,vol. 15, pp. 554- 557 ,(2013) , 10.1021/OL303371U
Kévin M. Joly, Claire Wilson, Alexander J. Blake, James H. R. Tucker, Christopher J. Moody, Competition between planar and central chiral control elements in nucleophilic addition to ferrocenyl imine derivatives Chemical Communications. pp. 5191- 5193 ,(2008) , 10.1039/B808045C
Nicolas Bragnier, Regis Guillot, Marie-Christine Scherrmann, Diastereoselective addition of sugar radicals to camphorsultam glyoxilic oxime ether: a route toward C-glycosylthreonine and allothreonine Organic and Biomolecular Chemistry. ,vol. 7, pp. 3918- 3921 ,(2009) , 10.1039/B910050D