Direct Synthesis of Vicinal Tricarbonyl Amides by Coupling of α-Oxo Acid Chlorides with Carbamoylsilanes

Abstract

A convenient synthetic method for vicinal tricarbonyl amides by the cross-coupling reaction of α-oxo acid chlorides with carbamoylsilanes is developed. The reaction tolerates a broad range of substituents on the amido nitrogen of carbamoylsilanes, and directly affords good yields of vicinal tricarbonyl amides under mild conditions without use of oxidants. The reaction of carbamoylsilanes with oxalyl chloride has also been explored, and is accompanied by decarbonylation to give vicinal tricarbonyl amides.

Key words

α-oxo acid chlorides - carbamoylsilanes - vicinal tricarbonyl compounds - aminocarbonylation - synthetic methods

• References

• 1a Adlington RM, Baldwin JE, Catterickand D, Pritchard GJ. J. Chem. Soc., Perkin Trans. 1 2001; 668
• 1b Altuna-Urquijo M, Gehre A, Stanforth SP, Tarbit B. Tetrahedron 2009; 65: 975
• 1c Wasserman HH, Rotello VM, Krause GB. Tetrahedron Lett. 1992; 33: 5419
• 1d Wasserman HH, Chenand JH, Xia M. J. Am. Chem. Soc. 1999; 121: 1401
• 1e Robach J, Baumeister J, Harms K, Koert U. Eur. J. Org. Chem. 2013; 662
• 1f Loosley BC, Andersen RJ, Dake GR. Org. Lett. 2013; 15: 1152
• 1g Robbach J, Harms K, Koert U. Eur. J. Org. Chem. 2014; 993
• 1h Robbach J, Harms K, Koert U. Org. Lett. 2015; 17: 3122
• 1i Yuki T, Yonekawa M, Matsumoto K, Sei Y, Tomita I, Endo T. Tetrahedron 2016; 65: 4783
• 1j Yuki T, Yonekawa M, Furusho Y, Sei Y, Tomita I, Endo T. Tetrahedron 2016; 65: 2868
• 2a Wasserman HH, Rotello VM. J. Org. Chem. 1989; 54: 2785
• 2b Jones TK, Mills SG, Reamer RA, Askin D, Desmond R, Volante RP, Shinkai I. J. Am. Chem. Soc. 1989; 111: 1157
• 2c Tanaka H, Kuroda A, Marusawa H, Hatanaka H, Kino T, Goto T, Hashimoto M, Taga T. J. Am. Chem. Soc. 1987; 109: 5031
• 2d Matsushita K, Suzuki K, Ohmori K. Synlett 2017; 28: 944
• 3a Rubin MB, Gleiter R. Chem. Rev. 2000; 100: 1121
• 3b Wasserman HH, Parr J. Acc. Chem. Res. 2004; 37: 687
• 3c Batchelor MJ, Gillespie RJ, Golec JM. C, Hedgecoch CJ. R. Tetrahedron Lett. 1993; 34: 167
• 3d Wasserman HH, Pichett JE. J. Am. Chem. Soc. 1982; 104: 4695
• 3e Asahara H, Nishiwaki N. J. Org. Chem. 2014; 79: 11735
• 3f Lai JH, Pham H, Hangauer DG. J. Org. Chem. 1996; 61: 1872
• 3g Santos MS, Coelho F. RSC Adv. 2012; 2: 3237
• 3h Wasserman HH, Ennis DS, Power PL, Ross MJ, Gomes B. J. Org. Chem. 1993; 58: 4785
• 3i Robbach J, Baumeister J, Harms K, Koert U. Eur. J. Org. Chem. 2013; 662
• 3j Hoffman RV, Kim HO, Wilson AL. J. Org. Chem. 1990; 55: 2820
• 3k Mahran MR, Abdou WM, Sidky MM, Wamhoff H. Synthesis 1987; 506
• 3l Lee K, Im JM. Tetrahedron Lett. 2001; 42: 1539
• 4a Baranac-Stojanovic M, Markovic R, Stojanovic M. Tetrahedron 2011; 67: 8000
• 4b Wang L.-Z, Li H.-L, Ge L.-S, An X.-L, Zhang Z.-G, Luo X, Fossey JS, Deng W.-P. J. Org. Chem. 2014; 79: 1156
• 4c Wang L.-Z, An X.-L, Ge L.-S, Jin J.-H, Luo X.-Y, Deng W.-P. Tetrahedron 2014; 70: 3788
• 4d Sivan A, Deepth A. Tetrahedron Lett. 2014; 55: 1890
• 4e Cui J, Duan Y.-N, Yu J, Zhang C. Org. Chem. Front. 2016; 3: 1686
• 4f Liu Y.-Y, Zhang Z.-G, Wan Y.-M, Zhang G.-S, Li Z.-L, Bi J.-G, Ma N.-N, Liu T.-X, Liu Q.-F. J. Org. Chem. 2017; 82: 3901
• 5a Tong W.-T, Liu H, Chen J.-X. Tetrahedron Lett. 2015; 56: 1335
• 5b Liu H, Guo Q.-L, Chen J.-X. Tetrahedron Lett. 2015; 56: 5747
• 5c Guo Q.-L, Wen X.-P, Chen J.-X. Tetrahedron 2016; 72: 8117
• 6a Cao P, Wen X.-P, Chen J.-X. Synlett 2017; 28: 353
• 6b Li W.-D, Han Y.-L, Chen J.-X. Tetrahedron 2017; 73: 5813
• 6c Yao Y, Li W.-D, Tong W.-T, Chen J.-X. Chin. J. Org. Chem. 2015; 35: 223
• 6d Li W.-D, Liu Y.-H, Chen J.-X. Tetrahedron Lett. 2015; 56: 4328
• 6e Yao Y, Li W.-D, Chen J.-X. Chin. J. Org. Chem. 2014; 34: 2124
• 6f Chen X.-J, Chen J.-X. Mendeleev Commun. 2013; 23: 106
• 7a Zhang W.-J, Han S.-H, Chen J.-X. Synth. Commun. 2017; 47: 704
• 7b Tong W.-T, Cao P, Liu Y.-H, Chen J.-X. J. Org. Chem. 2017; 82: 11603
• 7c Wen X.-P, Han Y.-L, Chen J.-X. RSC Adv. 2017; 7: 45107
• 7d Zhang W.-J, Cao P, Guo Q.-L, Chen J.-X. Curr. Org. Synth. 2017; 14: 1067
• 8 For the preparation of the carbamoylsilanes, see: Cunico RF, Chen J.-X. Synth. Commun. 2003; 33: 1963
• 9 Yonekawa M, Furusho Y, Sei Y, Takata T, Endo T. Tetrahedron 2013; 69: 4076
• 10 Schöllkopf U, Beckhaus H. Angew. Chem., Int. Ed. Engl. 1976; 15: 293
• 11 Davies SG, Ichihara O. Tetrahedron Lett. 1998; 39: 6045
• 12 Yuki T, Yonekawa M, Furusho Y, Sei Y, Tomita I, Endo T. Tetrahedron 2016; 72: 2868
• 13a Cunico RF, Motta AR. Org. Lett. 2005; 7: 771
• 13b Cunico RF, Pandey RK. J. Org. Chem. 2005; 70: 9048
• 14 Malmberg WD, Vob J, Weinschneider S. Liebigs Ann. Chem. 1983; 1694