Chemoselective, Isomerization-Free Synthesis of N -Acylketimines from N-H Imines
作者： Yearang Kwon , Young Ho Rhee , Jaiwook Park
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摘要: N-Acylketimines were synthesized through a ruthenium-catalyzed generation of N–H ketimines from secondary azides and subsequent acylation with mixed anhydrides under mild conditions. The synthetic scope was broad to give N-acylimines having various functional groups, including those aliphatic groups that are prone tautomerization the corresponding enamides. In addition, acyl moieties accommodated. utility this chemoselective imine illustrated by highly diastereoselective nucleophilic addition Grignard reagent cyclic N-acylimine.
sci-hub.se 参考文章(37)
Wook Jeong, Jungjoon Kim, Jaiwook Park, Young Ho Rhee, Stereoselective Synthesis of Highly Substituted α-Silylamines from Silylmethyl Azides under Ru Catalysis European Journal of Organic Chemistry. ,vol. 2014, pp. 7577- 7581 ,(2014) , 10.1002/EJOC.201403200
Gajendrasingh K. Ingle, Michael G. Mormino, Lukasz Wojtas, Jon C. Antilla, Chiral Phosphoric Acid-Catalyzed Addition of Thiols to N-Acyl Imines: Access to Chiral N,S-Acetals Organic Letters. ,vol. 13, pp. 4822- 4825 ,(2011) , 10.1021/OL201899C
Norie Momiyama, Hayato Nishimoto, Masahiro Terada, Chiral brønsted acid catalysis for enantioselective hosomi-sakurai reaction of imines with allyltrimethylsilane Organic Letters. ,vol. 13, pp. 2126- 2129 ,(2011) , 10.1021/OL200595B
Marino Petrini, α-Amido Sulfones as Stable Precursors of Reactive N-Acylimino Derivatives Chemical Reviews. ,vol. 105, pp. 3949- 3977 ,(2005) , 10.1021/CR050528S
Mina Jeon, Sreya Gupta, Young-Woong Im, Young Ho Rhee, Jaiwook Park, Fast and Complete Transimination of N ? H Imines into O‐Alkyl Oximes Asian Journal of Organic Chemistry. ,vol. 4, pp. 316- 319 ,(2015) , 10.1002/AJOC.201402293
Sarah Yunmi Lee, Jaclyn M. Murphy, Atsushi Ukai, Gregory C. Fu, Nonenzymatic Dynamic Kinetic Resolution of Secondary Alcohols via Enantioselective Acylation: Synthetic and Mechanistic Studies Journal of the American Chemical Society. ,vol. 134, pp. 15149- 15153 ,(2012) , 10.1021/JA307425G
Masato Uemura, Nobuhito Kurono, Takeshi Ohkuma, Enantioselective Hydrocyanation of N-Protected Aldimines Organic Letters. ,vol. 14, pp. 882- 885 ,(2012) , 10.1021/OL203408W
Jerry A. Murry, Doug E. Frantz, Arash Soheili, Richard Tillyer, Edward J. J. Grabowski, Paul J. Reider, Synthesis of α-amido ketones via organic catalysis: Thiazolium-catalyzed cross-coupling of aldehydes with acylimines [12] Journal of the American Chemical Society. ,vol. 123, pp. 9696- 9697 ,(2001) , 10.1021/JA0165943
Dong-gil Kim, Wook Jeong, Won Jong Lee, Soyeong Kang, Han Kyu Pak, Jaiwook Park, Young Ho Rhee, A Stereoselective Access to Cyclic cis‐1,2‐Amino Alcohols from trans‐1,2‐Azido Alcohol Precursors Advanced Synthesis & Catalysis. ,vol. 357, pp. 1398- 1404 ,(2015) , 10.1002/ADSC.201500267
Guilong Li, Frank R. Fronczek, Jon C. Antilla, Catalytic Asymmetric Addition of Alcohols to Imines: Enantioselective Preparation of Chiral N,O-Aminals Journal of the American Chemical Society. ,vol. 130, pp. 12216- 12217 ,(2008) , 10.1021/JA8033334