Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols
作者： Masatoshi Asami , Naomichi Miyairi , Yukihiro Sasahara , Ken-ichi Ichikawa , Naoya Hosoda
DOI: 10.1016/J.TET.2015.07.031
关键词: 1-Phenylethylamine 、 Pyrrolidine 、 Chemistry 、 Diethylzinc 、 Benzaldehyde 、 Catalysis 、 Organic chemistry 、 Cyclohexanone 、 Enantioselective synthesis
摘要: Abstract A series of o-xylylene-type 1,4-amino alcohols, synthesized from (R)-1-phenylethylamine, were used as chiral ligands for the enantioselective addition diethylzinc to benzaldehyde. (S)-1-Phenyl-1-propanol was obtained with high enantioselectivity in all cases since stereochemical outcome reaction controlled by benzylic carbon bearing amino group. Highest catalytic activity using (R)-1-{2-[1-(pyrrolidin-1-yl)ethyl]phenyl}cyclohexan-1-ol (1n) derived (R)-1-(1-phenylethyl)pyrrolidine and cyclohexanone. Various secondary alcohols aldehydes presence 1n within 2 h good enantioselectivities.
elsevier.com
sci-hub.se 参考文章(39)
Ryōji Noyori, Asymmetric catalysis in organic synthesis ,(1994)
Masatoshi Asami, Atsushi Nagai, Yukihiro Sasahara, Ken-ichi Ichikawa, Suguru Ito, Naoya Hosoda, Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Diastereomeric 1,4-Amino Alcohols with o-Xylylene Skeleton Chemistry Letters. ,vol. 44, pp. 345- 347 ,(2015) , 10.1246/CL.141113
Maya Marinova, Kalina Kostova, Pavleta Tzvetkova, Maya Tavlinova-Kirilova, Angel Chimov, Rosica Nikolova, Boris Shivachev, Vladimir Dimitrov, Synthesis of 1,3-aminonaphthols by diastereoselective Betti-type aminoalkylation of dihydroxy naphthalenes; diastereoselectivity, absolute configuration, and application Tetrahedron-asymmetry. ,vol. 24, pp. 1453- 1466 ,(2013) , 10.1016/J.TETASY.2013.09.023
Michał Rachwalski, Szymon Jarzyński, Stanisław Leśniak, Aziridine ring-containing chiral ligands as highly efficient catalysts in asymmetric synthesis Tetrahedron-asymmetry. ,vol. 24, pp. 421- 425 ,(2013) , 10.1016/J.TETASY.2013.03.001
Virginie Beaufort-Droal, Elisabeth Pereira, Vincent Théry, David J. Aitken, Preparation of non-racemic single-stereocentre α-aminonitriles and a study of their fate in Bruylants reactions Tetrahedron. ,vol. 62, pp. 11948- 11954 ,(2006) , 10.1016/J.TET.2006.09.087
Bing Zheng, Shuo-Ning Li, Jian-You Mao, Bo Wang, Qing-Hua Bian, Shang-Zhong Liu, Jiang-Chun Zhong, Hong-Chao Guo, Min Wang, Highly Enantioselective Addition of 1,3-Diynes to Aldehydes Catalyzed by a Zinc–Amino Alcohol Complex Chemistry: A European Journal. ,vol. 18, pp. 9208- 9211 ,(2012) , 10.1002/CHEM.201200728
David J. Ager, Indra Prakash, David R. Schaad, 1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis Chemical Reviews. ,vol. 96, pp. 835- 876 ,(1996) , 10.1021/CR9500038
M Haniti SA Hamid, C Liana Allen, Gareth W Lamb, Aoife C Maxwell, Hannah C Maytum, Andrew JA Watson, Jonathan MJ Williams, None, Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology. Journal of the American Chemical Society. ,vol. 131, pp. 1766- 1774 ,(2009) , 10.1021/JA807323A
Naoto Hanyu, Takashi Mino, Masami Sakamoto, Tsutomu Fujita, Facile synthesis of amino bicyclo[2.2.1]heptyl alcohol and its application for enantioselective additions of diethylzinc to aldehydes Tetrahedron Letters. ,vol. 41, pp. 4587- 4590 ,(2000) , 10.1016/S0040-4039(00)00637-7
Susan M. Lait, Danica A. Rankic, Brian A. Keay, 1,3-aminoalcohols and their derivatives in asymmetric organic synthesis. Chemical Reviews. ,vol. 107, pp. 767- 796 ,(2007) , 10.1021/CR050065Q