Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitro­styrenes

Abstract

A new reductive coupling reaction between N-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate–phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction with promising levels of enantioselectivity.

Key words

reduction - phosphates - nucleophilic addition - rearrangement - Michael addition

• References

• 1a Boeckman RK. Jr. Hudack RA. Jr. J. Org. Chem. 1998; 63: 3524
• 1b Jung M. Groth U. Synlett 2002; 2015
• 1c Groth U. Jung M. Vogel T. Chem. Eur. J. 2005; 11: 3127
• 1d Fischer S. Groth U. Jung M. Lindenmaier M. Vogel T. Tetrahedron Lett. 2005; 46: 6679
• 1e Miyoshi N. Fukuma T. Wada M. Chem. Lett. 1995; 999
• 2a Pudovik AN. Dokl. Akad. Nauk SSSR 1950; 73: 499 ; Chem. Abstr. 1951, 45, 2856
• 2b Galkin VI. Khabibullina AB. Bakhtiyarova IV. Cherkasov RA. Pudovik AN. Zh. Obshch. Khim. 1990; 60: 92
• 2c Sobanov AA. Zolotukhin AV. Galkina IV. Galkin VI. Cherkasov RA. Russ. J. Gen. Chem. 2006; 76: 421
• 2d Sobanov AA. Zolotukhin AV. Galkin VI. Mostovaya OA. Cherkasov RA. Pudovik AN. Russ. J. Gen. Chem. 2003; 73: 871
• 2e Sobanov AA. Zolotukhin AV. Galkin VI. Cherkasov RA. Pudovik AN. Russ. J. Gen. Chem. 2002; 72: 1067
• 2f Albouy D. Lasperas M. Etemad-Moghadam G. Koenig M. Tetrahedron Lett. 1999; 40: 2311
• 2g Qian CT. Huang TS. Fenzi Cuihua 1997; 11: 455
• 2h Yokomatsu T. Yamagishi T. Shibuya S. J. Chem. Soc., Perkin Trans. 1 1997; 1527
• 2i Groeger H. Wilken J. Martens J. Z. Naturforsch., B: Chem. Sci. 1996; 51: 1305
• 2j Ovchinnikov VV. Zh. Obshch. Khim. 1996; 66: 463
• 2k Groeger H. Martens J. Synth. Commun. 1996; 26: 1903
• 2l Safina YuG. Malkova GSh. Cherkasov RA. Zh. Obshch. Khim. 1991; 61: 620
• 2m Galkin VI. Galkina IV. Khabibullina AB. Al Kurdi H. Cherkasov RA. Pudovik AN. Dokl. Akad. Nauk SSSR 1990; 314: 1408
• 2n Nesterov LV. Krepysheva NE. Aleksandrova NA. Zh. Obshch. Khim. 1984; 54: 54
• 2o Malenko DM. Gololobov YuG. Zh. Obshch. Khim. 1978; 48: 2793
• 2p Abramov VS. Dokl. Akad. Nauk SSSR 1950; 73: 487 ; Chem. Abstr. 1951, 45, 2855
• 2q Chen SJ. Coward JK. J. Org. Chem. 1998; 63: 502
• 2r Gawron O. Grelecki C. Reilly W. Sands J. J. Am. Chem. Soc. 1953; 75: 3591
• 2s Tongcharoensirikul P. Suarez AI. Voelker T. Thompson CM. J. Org. Chem. 2004; 69: 2322
• 3a Kondoha A. Terada M. Org. Chem. Front. 2015; 2: 801
• 3b Fitch SJ. Moedritzer K. J. Am. Chem. Soc. 1962; 84: 1876
• 3c Hall LA. R. Stephens CW. Drysdale JJ. J. Am. Chem. Soc. 1957; 79: 1768
• 3d Kuroboshi M. Ishihara T. Ando T. J. Fluorine Chem. 1988; 39: 293
• 3e Demir AS. Reis Ö. İğdir A. Ç. Esiringü İ. Eymur S. J. Org. Chem. 2005; 70: 10584
• 3f Demir AS. Reis B. Reis Ö. Eymür S. Göllü M. Tural S. Saglam G. J. Org. Chem. 2007; 72: 7439
• 3g Demir AS. Esiringü l. Göllü M. Reis Ö. J. Org. Chem. 2009; 74: 2197
• 3h Kondoh A. Terada M. Org. Lett. 2013; 15: 4568
• 3i Pallikonda G. Santosh R. Ghosal S. Chakravarty M. Tetrahedron Lett. 2015; 56: 3796
• 3j Kondoh A. Ishikawa S. Aoki T. Terada M. Chem. Commun. 2016; 52: 12513
• 3k Kondoh A. Takei A. Terada M. Synlett 2016; 27: 1848
• 3l Kondoh A. Aoki T. Terada M. Org. Lett. 2014; 16: 3528
• 4a Horwitz MA. Zavesky BP. Martinez-Alvarado JI. Johnson JS. Org. Lett. 2016; 18: 36
• 4b Horwitz MA. Tanaka N. Yokosaka T. Uraguchi D. Johnson JS. Ooi T. Chem. Sci. 2015; 6: 6086
• 4c Corbett M. Uraguchi D. Ooi T. Johnson JS. Angew. Chem. Int. Ed. 2012; 51: 4685
• 4d Bausch CC. Johnson JS. Adv. Synth. Catal. 2005; 347: 1207
• 5a Kondoh A. Terada M. Org. Biomol. Chem. 2016; 14: 4704
• 5b Jiang J. Liu H. Lu C.-D. Xu Y.-J. Org. Lett. 2016; 18: 880
• 6 Yin D. Liu H. Lu C.-D. Xu Y.-J. J. Org. Chem. 2017; 82: 3252
• 7a Stivala CE. Zakarian A. J. Am. Chem. Soc. 2011; 133: 11936
• 7b Frizzle MJ. Caille S. Marshall TL. McRae K. Nadeau K. Guo G. Wu S. Martinelli MJ. Moniz GA. Org. Process Res. Dev. 2007; 11: 215
• 8 CCDC 1530988 (4aa) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures
• 9a Vakulya B. Varga S. Csampai A. Soos T. Org. Lett. 2005; 7: 1967
• 9b Rong Z.-Q. Pan H.-J. Yan H.-L. Zhao Y. Org. Lett. 2014; 16: 208
• 9c Yang W. Du D.-M. Org. Lett. 2010; 12: 5450
• 9d Manna MS. Kumar V. Mukherjee S. Chem. Commun. 2012; 48: 5193
• 9e Núñez MG. Farley AJ. M. Dixon DJ. J. Am. Chem. Soc. 2013; 135: 16348
• 10a Overman LE. Peterson EA. Tetrahedron 2003; 59: 6905
• 10b Vyas DJ. Froehlich R. Oestreich M. J. Org. Chem. 2010; 75: 6720
• 10c Bouhfid R. Joly N. Essassi EM. Lequart V. Massoui M. Martin P. Synth. Commun. 2011; 41: 2096
• 11a Hashmi AS. K. Häffner T. Yang W. Pankajakshan S. Schäfer S. Schultes L. Rominger F. Frey W. Chem. Eur. J. 2012; 18: 10480
• 11b Ashokkumar V. Siva A. Org. Biomol. Chem. 2015; 13: 10216
• 11c Xu C. Du J. Ma L. Li G. Tao M. Zhang W. Tetrahedron 2013; 69: 4749
• 11d Quan X.-J. Ren Z.-H. Wang Y.-Y. Guan Z.-H. Org. Lett. 2015; 17: 393
• 11e Kolarovic A. Käslin A. Wennemers H. Org. Lett. 2014; 16: 4236
• 11f Park J.-e. Song C. Choi K. Sim T. Moon B. Roh EJ. Bioorg. Med. Chem. Lett. 2013; 23: 5515
• 11g McNulty J. Steere JA. Wolf S. Tetrahedron Lett. 1998; 39: 8013
• 11h Chen J. Geng Z.-C. Li N. Huang X.-F. Pan F.-F. Wang X.-W. J. Org. Chem. 2013; 78: 2362