Efficient synthesis of α-amino acid derivatives via phase-transfer-catalyzed directed reductive amination

Xiaohua Zhang , Wenjing Ye , Kuanglei Wang , Yongshou Tian , Xiao Xiao

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (2) : 203 -207.

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Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (2) : 203 -207. DOI: 10.1007/s40242-015-4412-z
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Efficient synthesis of α-amino acid derivatives via phase-transfer-catalyzed directed reductive amination

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Abstract

An efficient phase-transfer-catalyzed directed reductive amination of α-keto esters was described using simple substituted benzyl amines as nitrogen source and K2CO3 as base at room temperature, giving a series of aliphatic α-amino acid derivatives in moderate to high yields(up to 99%). Preliminary study on this asymmetric process showed that cinchona-derived phase transfer catalyst was effective, affording the corresponding product in 13% e.e. and 40% yield.

Keywords

Directed reductive amination / α-Amino acid / Phase transfer catalyst

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Xiaohua Zhang, Wenjing Ye, Kuanglei Wang, Yongshou Tian, Xiao Xiao. Efficient synthesis of α-amino acid derivatives via phase-transfer-catalyzed directed reductive amination. Chemical Research in Chinese Universities, 2015, 31(2): 203-207 DOI:10.1007/s40242-015-4412-z

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References

[1]

Abdel-Magid A F, Carson K G, Harris B D, Maryanoff C A, Shah R D. J. Org. Chem., 1996, 61(11): 3849.

[2]

Gomez S, Peters J A, Maschmeyer T. Adv. Synth. Catal., 2002, 344(10): 1037.

[3]

Tararov V I, Börner A. Synlett., 2005, 203.

[4]

Nugent T C, El-Shazlya M. Adv. Synth. Catal., 2010, 352(5): 753.

[5]

Wang C, Xiao J. Top. Curr. Chem., 2014, 343: 261.

[6]

Kitamura M, Lee D, Hayashi S, Tanaka S, Yoshimura M. J. Org. Chem., 2002, 67(24): 8685.

[7]

Ogo S, Uehara K, Abura T, Fukuzumi S. J. Am. Chem. Soc., 2004, 126(10): 3020.

[8]

Murahashi S I, Watanabe S, Shiota T. Chem. Commun., 1994, 725.

[9]

Kadyrov R, Riermeier T H, Dingerdissen U, Tararov V, Börner A. J. Org. Chem., 2003, 68(10): 4067.

[10]

Martell A E. Acc. Chem. Res., 1989, 22(4): 115.

[11]

Guthrie R D, Jaeger D A, Meister W, Cram D J. J. Am. Chem. Soc., 1971, 93(20): 5137.

[12]

Jaeger D A, Cram D J. J. Am. Chem. Soc., 1971, 93(20): 5153.

[13]

Hughes A B. Amino Acids, Peptides and Proteins in Organic Chemistry, 2009, Weinheim: Wiley-VCH.

[14]

Kuzuhara H, Komatsu T, Emoto S. Tetrahedron Lett., 1978, 19(38): 3563.

[15]

Breslow R. Acc. Chem. Res., 1995, 28(3): 146.

[16]

Murakami Y, Kikuchi J, Hisaeda Y, Hayashida O. Chem. Rev., 1996, 96(2): 721.

[17]

Han J, Sorochinsky A E, Ono T, Soloshonok V A. Curr. Org. Synth., 2011, 8(2): 281.

[18]

Hjelmencrantz A, Berg U. J. Org. Chem., 2002, 67(11): 3585.

[19]

Knudsen K R, Bachmann S, Jørgensen K A. Chem. Commun., 2003, 2602.

[20]

Bachmann S, Knudsen K R, Jørgensen K A. Org. Biomol. Chem., 2004, 2(14): 2044.

[21]

Xiao X, Xie Y, Su C, Liu M, Shi Y. J. Am. Chem. Soc., 2011, 133(33): 12914.

[22]

Xiao X, Liu M, Rong C, Xue F, Li S, Xie Y, Shi Y. Org. Lett., 2012, 14(20): 5270.

[23]

Su C, Xie Y, Pan H, Liu M, Tian H, Shi Y. Org. Biomol. Chem., 2014, 12(31): 5856.

[24]

Liu M, Li J, Xiao X, Xie Y, Shi Y. Chem. Commun., 2013, 1404.

[25]

Xie Y, Pan H, Xiao X, Li S, Shi Y. Org. Biomol. Chem., 2012, 10(45): 8960.

[26]

Pan H, Xie Y, Liu M, Shi Y. RSC Adv., 2014, 4(5): 2389.

[27]

Xue F, Xiao X, Wang H, Shi Y. Tetrahedron, 2012, 68(34): 6862.

[28]

Shi Y, Xue F, Xiao X. A Method of the Synthesis of α-Amino Esters, 2012.

[29]

Pierrick N, Violaine P, Monique C, Jean M, Frederic L. Chem. Eur. J., 2012, 18(12): 3773.

[30]

Jew S, Park H. Chem. Commun., 2009, 7090.

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