Recent Developments in Nitrone Chemistry: Some Novel Transformations

Jiong Yang

doi:10.1055/s-0032-1317096

Synlett, Table of Contents

Synlett 2012; 23(16): 2293-2297
DOI: 10.1055/s-0032-1317096

synpacts

Recent Developments in Nitrone Chemistry: Some Novel Transformations

Authors

Jiong Yang*

Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, USA, Fax: +1(979)8454719 Email: yang@mail.chem.tamu.edu

Abstract

All articles of this category

Abstract

Despite the long history of nitrone chemistry, novel transformations of nitrones continue to be discovered. This article describes some recent breakthroughs in the development of new transformations of nitrones. These new reactions include formal [3+3] cycloaddition of nitrones and vinylcarbenes to give 3,6-dihydro-1,2-oxazines, tandem cyclization–[3+3] cycloaddition of nitrones and enynones to give furo[3,4-d][1,2]oxazines, [2+2+3] cycloaddition of nitrones and 1,6-enynes to give tricyclic 1,2-oxazepanes, reaction of nitrones and 2-azido acrylates to form 1,2,4,5-tetrasubstituted imidazoles, and reactions of α,β-unsaturated N-aryl ketonitrones and activated alkynes to generate C3-quaternary indolenines.

Key words

nitrone - dipolar cycloaddition - tandem reaction - catalysis - indolenine

Full Text

References

References

For some early reviews:

1a Huisgen R. Angew. Chem. Int. Ed. Engl. 1963; 2: 565
1b Smith LI. Chem. Rev. 1938; 38: 193
1c Hamer J, Macaluso A. Chem. Rev. 1964; 64: 473

2 For an excellent review of nucelophilic additions to chiral nitrones, see : Merino P, Franco S, Merchan FL, Tejero T. Synlett 2000; 442

3a Cardona F, Goti A. Angew. Chem. Int. Ed. 2005; 44: 7832
3b Marco-Contelles J. Angew. Chem. Int. Ed. 2004; 43: 2198

4a Masson G, Cividino P, Py S, Vallée Y. Angew. Chem. Int. Ed. 2003; 42: 2265
4b Riber D, Skrydstrup T. Org. Lett. 2003; 5: 229
4c Cividino P, Py S, Delair P, Greene AE. J. Org. Chem. 2007; 72: 485

For the initial report, see:

5a Kinugasa M, Hashimoto S. J. Chem. Soc., Chem. Commun. 1972; 466

For examples of catalytic asymmetric versions, see:

5b Miura M, Enna M, Okuro K, Nomura M. J. Org. Chem. 1995; 60: 4999
5c Lo MM.-C, Fu GC. J. Am. Chem. Soc. 2002; 124: 4572
5d Shintani R, Fu GC. Angew. Chem. Int. Ed. 2003; 42: 4082
5e Ye M.-C, Zhou J, Huang Z.-Z, Tang Y. Chem. Commun. 2003; 2554
5f Ye M.-C, Zhou J, Tang Y. J. Org. Chem. 2006; 71: 3576
5g Basak A, Ghosh SC. Synlett 2004; 1637
5h Coyne AG, Mueller-Bunz H, Guiry PJ. Tetrahedron: Asymmetry 2007; 18: 199
5i Evans DA, Kleinbeck F, Ruping M In Asymmetric Synthesis: The Essentials . Christmann M, Bräse S. Wiley-VCH; Weinheim: 2007: 72
5j Saito T, Kikuchi T, Tanabe H, Yahiro J, Otani T. Tetrahedron Lett. 2009; 50: 4969
5k Chen J.-H, Liao S.-H, Sun X.-L, Shen Q, Tang Y. Tetrahedron Lett. 2012; 68: 5042

The formal [3+3] cycloaddition of nitrones and 1,1-cyclopropane diesters was also designated as homo [3+2] dipolar cycloaddition:

6a Young IS, Kerr MA. Angew. Chem. Int. Ed. 2003; 42: 3023
6b Young IS, Kerr MA. Org. Lett. 2004; 6: 139
6c Ganton MD, Kerr MA. J. Org. Chem. 2004; 69: 8554
6d Young IS, Williams JL, Kerr MA. Org. Lett. 2005; 7: 953
6e Carson CA, Kerr MA. Angew. Chem. Int. Ed. 2006; 45: 6560
6f Sibi MK, Mz Z, Jasperse CP. J. Am. Chem. Soc. 2005; 127: 5764
6g Kang Y.-B, Sun X.-L, Tang Y. Angew. Chem. Int. Ed. 2007; 46: 3918

For related Pd-catalyzed formal [3+3] and [4+3] cycloaddition of N,α-diarylnitrones, see:

6h Shintani R, Hayashi T. J. Am. Chem. Soc. 2006; 128: 6330
6i Shintani R, Park S, Duan W.-L, Hayashi T. Angew. Chem. Int. Ed. 2007; 46: 5901
6j Shintani R, Murakami M, Hayashi T. J. Am. Chem. Soc. 2007; 129: 12356

7 Stevens AC, Palmer C, Pagenkopf BL. Org. Lett. 2011; 13: 1528
8 Wang X, Xu X, Zavalij PY, Doyle MP. J. Am. Chem. Soc. 2011; 133: 16402
9 Qian Y, Xu X, Wang X, Zavalij PJ, Hu W, Doyle MP. Angew. Chem. Int. Ed. 2012; 51: 5900
10 Xu X, Ratnikov MO, Zavalij PY, Doyle MP. Org. Lett. 2011; 13: 6122
11 Wang X, Abrahams QM, Zavalij PY, Doyle MP. Angew. Chem. Int. Ed. 2012; 51: 5907

12a Liu F, Yu Y, Zhang J. Angew. Chem. Int. Ed. 2009; 48: 5505
12b Liu F, Qian D, Li L, Zhao X, Zhang J. Angew. Chem. Int. Ed. 2010; 49: 6669

For some related transformations, see:

13a Zhang Y, Liu F, Zhang J. Chem. Eur. J. 2010; 6: 6146
13b Wang T, Zhang J. Chem. Eur. J. 2011; 17: 86
13c Bai Y, Fang J, Ren J, Wang Z. Chem. Eur. J. 2009; 15: 8975

14 Gawade SA, Bhunia S, Liu R.-S. Angew. Chem. Int. Ed. 2012; 51: 7835
15 Hu B, Wang Z, Ai N, Zheng J, Liu X.-H, Shan S, Wang Z. Org. Lett. 2011; 13: 6362

16a Pfeiffer JY, Beauchemin AM. J. Org. Chem. 2009; 74: 8381
16b Franco S, Merchan FL, Merino P, Tejero T. Synth. Commun. 1995; 25: 2272

17a Bartoli G, Marcantoni E, Petrini M. J. Org. Chem. 1990; 55: 4456
17b Bartoli G, Petrini M, Marcantoni E, Bosco M, Dalpozzo R. Tetrahedron Lett. 1990; 31: 6089
17c Bartoli G, Marcantoni E, Petrini M. J. Chem. Soc., Chem. Commun. 1991; 793

18 Hood, T. S.; Huehls, C. B.; Yang, J. unpublished results.
19 Tian G.-Q, Yang J, Rosa-Perez K. Org. Lett. 2010; 12: 5072
20 Hood TS, Huehls CB, Yang J. Tetrahedron Lett. 2012; 53: 4679

For some examples of indolenines in syntheses of indole-containing natural products, see:

21a Robinson R, Suginome H. J. Chem. Soc. 1932; 298
21b Woodward RB, Cava MP, Ollis WD, Hunger A, Daeniker HU, Schenker K. J. Am. Chem. Soc. 1954; 76: 4749
21c Stork G, Dolfini JE. J. Am. Chem. Soc. 1963; 85: 2872
21d He F, Bo Y, Altom JD, Corey EJ. J. Am. Chem. Soc. 1999; 121: 6771
21e Kozmin SA, Iwama T, Huang Y, Rawal VH. J. Am. Chem. Soc. 2002; 124: 4628

22 Huehls CB, Hood TS, Yang J. Angew. Chem. Int. Ed. 2012; 51: 5110
23 Hoffmann R. Chem. Rev. 1989; 89: 1841