Amino acid homologation by the Blaise reaction: a new entry into nitrogen heterocycles.
作者： Cam Thuy Hoang , Francelin Bouillère , Sine Johannesen , Anaïs Zulauf , Cécilia Panel
DOI: 10.1021/JO900324D
关键词:
摘要: A general strategy for the amino acid homologation via Blaise reaction and subsequent reduction is presented. This involves preparation of protected α-amino nitriles from corresponding acids, followed by zinc-mediated condensation tert-butyl bromoacetate, to give imidazolidones after iminozincate cyclization. Reduction gave saturated imidazolidinones with cis or trans stereochemistry, depending on conditions. was applied nonfunctionalized acids functionalized such as serine aspartic acid. Additionally, acidic hydrolysis chiral 4-aminopyrrolidones described.
acs.org
core.ac.uk 
sci-hub.se 参考文章(69)
Klaus Hofmann, Donald B. Melville, Vincent du Vigneaud, CHARACTERIZATION OF THE FUNCTIONAL GROUPS OF BIOTIN Journal of Biological Chemistry. ,vol. 141, pp. 207- 214 ,(1941) , 10.1016/S0021-9258(18)72835-4
Qian Dai, Weiran Yang, Xumu Zhang, Efficient Rhodium-Catalyzed Asymmetric Hydrogenation for the Synthesis of a New Class ofN-Aryl β-Amino Acid Derivatives Organic Letters. ,vol. 7, pp. 5343- 5345 ,(2005) , 10.1021/OL0523897
D. Misiti, M. Santaniello, G. Zappia, Synthesis of (3R)- and (3S)-3,4-Diamino-Butyric Acid from L-Aspartic Acid Synthetic Communications. ,vol. 22, pp. 883- 891 ,(1992) , 10.1080/00397919208020852
Giuseppina Calvisi, Natalina Dell’Uomo, Francesco De Angelis, Roberto Dejas, Fabio Giannessi, Maria Ornella Tinti, A Practical and Stereoconservative Synthesis of (R)-3-Amino-4-(trimethylammonio)butanoate [(R)-Aminocarnitine], and Its Trimethylphosphonium and Simple Ammonium Analogues Starting from D-Aspartic Acid European Journal of Organic Chemistry. ,vol. 2003, pp. 4501- 4505 ,(2003) , 10.1002/EJOC.200300428
Yi Hsiao, Nelo R. Rivera, Thorsten Rosner, Shane W. Krska, Eugenia Njolito, Fang Wang, Yongkui Sun, Joseph D. Armstrong, Edward J. J. Grabowski, Richard D. Tillyer, Felix Spindler, Christophe Malan, Highly Efficient Synthesis of β-Amino Acid Derivatives via Asymmetric Hydrogenation of Unprotected Enamines Journal of the American Chemical Society. ,vol. 126, pp. 9918- 9919 ,(2004) , 10.1021/JA047901I
Marc Mauduit, Cyrille Kouklovsky, Yves Langlois, Oxazoline N-Oxide Mediated [3+2] Cycloadditions: Application to a Formal Synthesis of a (+)-β-Methylcarbapenem European Journal of Organic Chemistry. ,vol. 2000, pp. 1595- 1601 ,(2000) , 10.1002/(SICI)1099-0690(200004)2000:8<1595::AID-EJOC1595>3.0.CO;2-E
Richard F. Borch, Mark D. Bernstein, H. Dupont Durst, Cyanohydridoborate anion as a selective reducing agent Journal of the American Chemical Society. ,vol. 93, pp. 2897- 2904 ,(1971) , 10.1021/JA00741A013
Dongwon Yoo, Seah Kwon, Young Gyu Kim, Application of the N-hydroxymethyl group to the stereoselective synthesis of (3S,4S)-3-aminodeoxystatine derivatives Tetrahedron-asymmetry. ,vol. 16, pp. 3762- 3766 ,(2005) , 10.1016/J.TETASY.2005.10.018
Jae Hoon Lee, Bo Seung Choi, Jay Hyok Chang, Hee Bong Lee, Joo-Yong Yoon, Jaeick Lee, Hyunik Shin, None, The decarboxylative Blaise reaction. Journal of Organic Chemistry. ,vol. 72, pp. 10261- 10263 ,(2007) , 10.1021/JO701743M
Jana Syed, Siegfried Förster, Franz Effenberger, Application of the Blaise reaction: stereoselective synthesis of (4R)-tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates from (R)-cyanohydrins Tetrahedron-asymmetry. ,vol. 9, pp. 805- 815 ,(1998) , 10.1016/S0957-4166(98)00039-1