Synlett 2019; 30(10): 1241-1245
DOI: 10.1055/s-0037-1610713
letter
© Georg Thieme Verlag Stuttgart · New York

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

Haiyan Wu
,
Hongxin Liu
,
Juan Li
,
Xinhua Li*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: lixinhua01@126.com   Email: junjiang@wzu.edu.cn
,
Hong-Ping Xiao
,
Jun Jiang*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: lixinhua01@126.com   Email: junjiang@wzu.edu.cn
› Author Affiliations
We are grateful for financial support from National Natural Science Foundation of China (NSFC, Grant No. 21472141 and 21571144) and Natural Science Foundation of Zhejiang Province (Grant No. LY18B020011 and LQ19B020004).
Further Information

Publication History

Received: 03 March 2019

Accepted after revision: 24 April 2019

Publication Date:
08 May 2019 (online)


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.

Supporting Information

 
  • 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