CiteScore: 1.9     h-index: 21

Document Type : Original Research Article

Authors

1 Department of Chemistry, Dnyanopasak College, Parbhani-431 401, MS, India

2 Department of Chemistry, Dnyanopasak College, Parbhani-431401, MS, India

Abstract

An effective protocol for the asymmetric synthesis of β-amino carbonyl compounds using pyrrolidine based organocatalyst has been developed via one-pot three-component Mannich reaction. The organocatalyst (S)-N-(2,4-dinitrophenyl) pyrrolidine-2-carboxamide 3b confirmed to be the superior organocatalyst in solvent acetonitrile to obtain corresponding products in up to 89% yield and with excellent ee (90%). This organocatalytic reaction reveals productive result with a range of other aldehydes. Aromatic aldehydes having electron withdrawing substituent show the best results. Excellent yields, high enantioselectivity, mild reaction condition, and simple experimental work-up procedure are some of the advantages of this method.

Graphical Abstract

Organocatalytic enantioselective one-pot synthesis of β-aminoketones via Mannich reaction

Keywords

[1]. Mannich C., Krosche W. Arch. Pharm., 1912, 250:647
[2]. Cordova A. Acc. Chem. Res., 2004, 37:102
[3]. Kobayashi S., Mori Y., Fossey J.S., Salter M.M. Chem. Rev., 2011, 111:2626
[4]. Ting A., Schaus S.E. Eur. J. Org. Chem., 2007, 2007:5797
[5]. Friestad G.K., Mathies A.K. Tetrahedron, 2007, 63:2541
[6]. Kobayashi S., Kobayashi J., Yazaki R., Ueno M. Chem. Asian J., 2007, 2:135
[7]. Kobayashi S., Yazaki R., Seki K., Ueno M. Tetrahedron, 2007, 63:8425
[8]. Salter M.M., Kobayashi J., Shimizu Y., Kobayashi S. Org. Lett., 2006, 8:3533
[9]. Kobayashi S., Kobayashi J., Ishitani H., Ueno M. Chem. Eur. J., 2002, 8:4185
[10]. Wu C., Fu X., Li S. Tetrahedron: Asymmetry, 2011, 22:1063
[11]. Wu C., Fu X., Ma X., Li S., Li C. Tetrahedron Lett., 2010, 51:5775
[12]. Izumiseki A., Yoshida K., Yanagisawa A. Org. Lett., 2009, 11:5310
[13]. List B., Pojarliev P., Biller W.T., Martin H.J. J. Am. Chem. Soc., 2002, 124:827
[14]. Ibrahem I., Zou W., Engqvist M., Xu Y., Cordova A. Chem. Eur. J., 2005, 11:7024
[15]. Mousavi M.R., Hazeri N.,  Maghsoodlou M.T.,  Salahi S., Habibi-Khorassani S.M. Chin. Chem. Lett., 2013, 24:411
[16]. Maghsoodlou M.T., Khorshidi N., Mousavi M.R., Hazeri N., Habibi-Khorassani S.M. Res. Chem. Intermed., 2015, 41:7497
[17]. Mousavi M.R., Maghsoodlou M.T., Hazeri N., Aboonajmi J., Habibi-Khorassani S.M. Iran. J. Org. Chem., 2014,6:1323
[18]. Maghsoodlou M.T., Mousavi S.R., Roygar A., Lashkari M. Kragujevac J. Sci., 2018, 40:71
[19]. Goswami S.V., Thorat P.B., Chakrawar A.V., Bhusare S.R. Mol. Divers., 2013, 17:33
[20]. Ollevier T., Nadeau E., Guay-Be´gin A.A. Tetrahedron Lett., 2006, 47:8351
[21]. Li H., Zeng H., Shao H. Tetrahedron Lett., 2009, 50:6858
[22]. He T., Li K., Wu M.Y., Feng X.W., Wang N., Wang H.Y., Li C., Yu X.Q. J. Mol. Catal. B: Enzym., 2010, 67:189
[23]. Thorat P.B., Goswami S.V., Khade B.C., Bhusare S.R. Tetrahedron Asymmetry, 2012, 23:1320
[24]. Thorat P.B., Goswami S.V., Khade B.C., Bhusare S.R. Tetrahedron Lett., 2012, 53:6083
[25]. Pendalwar S.S., Chakrawar A.V., Bhusare S.R. Chin. Chem. Lett., 2018, 29:942