Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles

Abstract

The exploration of catalytic potential of natural amino acid salt in activation of 1,3-dicarbonyls was carried out, in which maleimides and 2-(2-oxoindolin-3-ylidene)malononitriles were found to be good electrophiles and afforded the desired products with excellent yield and moderate optical purity. Control experiments showed that the secondary amino group of barium (S)-prolinate is critical to the catalytic activity as well as enantiocontrol, thus revealed an enamine activation mechanism is possible in the present methodology.

Key words

natural amino acid salt - 1,3-dicarbonyls - asymmetric catalysis - addition reaction

• References and Notes


For reviews, see:
• 1a Volla CM. R, Atodiresei I, Rueping M. Chem. Rev. 2014; 114: 2390
• 1b Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
• 2 Benetti S, Romagnoli R, De Risi C, Spalluto G, Zanirato V. Chem. Rev. 1995; 95: 1065

For reviews, see:
• 3a Govender T, Arvidsson PI, Maguire GE. M, Kruger HG, Naicker T. Chem. Rev. 2016; 116: 9375
• 3b Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713

For reviews, see:
• 4a Erkkilä A, Majander I, Pihko PM. Chem. Rev. 2007; 107: 5416
• 4b Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
• 5 For a review, see: Zhang L, Fu N, Luo S. Acc. Chem. Res. 2015; 48: 986
• 6a Zhou P, Zhang L, Luo S, Cheng J.-P. J. Org. Chem. 2012; 77: 2526
• 6b Xu C, Zhang L, Zhou P, Luo S, Cheng J.-P. Synthesis 2013; 45: 1939
• 6c Xu C, Zhang L, Luo S. J. Org. Chem. 2014; 79: 11517
• 6d Xu C, Zhang L, Luo S. Angew. Chem. Int. Ed. 2014; 53: 4149
• 6e Wang D, Xu C, Zhang L, Luo S. Org. Lett. 2015; 17: 576
• 6f Zhu Y, Zhang L, Luo S. J. Am. Chem. Soc. 2014; 136: 14642
• 7a Kang G, Luo Z, Liu C, Gao H, Wu Q, Wu H, Jiang J. Org. Lett. 2013; 15: 4738
• 7b Wu Q, Liu S, Wang F, Li Q, Chen K, Li J, Jiang J. Synlett 2015; 26: 2442

For a review, see:
• 8a Mlynarski J, Paradowska J. Chem. Soc. Rev. 2008; 37: 1502

For selected examples, see:
• 8b Darbre T, Machuqueiro M. Chem. Commun. 2003; 1090
• 8c Fernandez-Lopez R, Kofoed J, Machuqueiro M, Darbre T. Eur. J. Org. Chem. 2005; 5268
• 8d Kofoed J, Darbre T, Reymond JL. Chem. Commun. 2006; 1482
• 8e Itoh S, Kitamura M, Yamada Y, Aoki S. Chem. Eur. J. 2009; 15: 10570
• 8f Karmakar A, Maji T, Wittmann S, Reiser O. Chem. Eur. J. 2011; 17: 11024

For amino acid salts catalyzed Robinson annulation, see:
• 8g Li P.-F, Yamamoto H. Chem. Commun. 2009; 5412
• 9a Yamaguchi M, Shiraishi T, Hirama M. Angew. Chem., Int. Ed. Engl. 1993; 32: 1176
• 9b Yamaguchi M, Shiraishi T, Hirama M. J. Org. Chem. 1996; 61: 3520
• 9c Sato A, Yoshida M, Hara S. Chem. Commun. 2008; 6242
• 9d Yoshida M, Narita M, Hirama K, Hara S. Tetrahedron Lett. 2009; 50: 7297
• 9e Yoshida M, Sato A, Hara S. Org. Biomol. Chem. 2010; 8: 3031
• 9f Yoshida M, Kitamikado N, Ikehara H, Hara S. J. Org. Chem. 2011; 76: 2305
• 9g Yoshida M, Hirama K, Narita M, Hara S. Symmetry 2011; 3: 155
• 9h Yoshida M, Narita M, Hara S. J. Org. Chem. 2011; 76: 8513
• 9i Yoshida M, Masaki E, Ikehara H, Hara S. Org. Biomol. Chem. 2012; 10: 5289
• 9j Xu K, Zhang S, Hu Y, Zha Z, Wang Z. Chem. Eur. J. 2013; 19: 3573
• 10 Liu XH, Qin B, Zhou X, He B, Feng XM. J. Am. Chem. Soc. 2005; 127: 12224

For examples of catalytic asymmetric addition reaction of 1,3-dicarbonyls to maleimide, see:
• 11a Ye W, Jiang Z, Zhao Y, Goh SL. M, Leow D, Soh Y.-T, Tan C.-H. Adv. Synth. Catal. 2007; 349: 2454
• 11b Gómez-Torres E, Alonso DA, Gómez-Bengoa E, Nájera C. Org. Lett. 2011; 13: 6106
• 12a Chen W.-B, Wu Z.-J, Pei Q.-L, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett. 2010; 12: 3132
• 12b Jiang X, Sun Y, Yao J, Cao Y, Kai M, He N, Zhang X, Wang Y, Wang R. Adv. Synth. Catal. 2012; 354: 917