N-Heterocyclic Carbene-Catalyzed Vinylogous Mukaiyama Aldol Reaction of α-Keto Esters and α-Trifluoromethyl Ketones

Ying Wang; Fen Xing; Mei Xue; Guang-Fen Du; Xu-Hong Guo; Kuo-Wei Huang; Bin Dai

doi:10.1055/s-0035-1560833

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(01): 79-84
DOI: 10.1055/s-0035-1560833

paper

N-Heterocyclic Carbene-Catalyzed Vinylogous Mukaiyama Aldol Reaction of α-Keto Esters and α-Trifluoromethyl Ketones

Ying Wang

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China eMail: duguangfen@shzu.edu.cn

,

Fen Xing

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China eMail: duguangfen@shzu.edu.cn

,

Mei Xue

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China eMail: duguangfen@shzu.edu.cn

,

Guang-Fen Du*

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China eMail: duguangfen@shzu.edu.cn

^bLaboratory of Materials-Oriented Chemical Engineering of Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China

,

Xu-Hong Guo

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China eMail: duguangfen@shzu.edu.cn

^bLaboratory of Materials-Oriented Chemical Engineering of Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China

,

Kuo-Wei Huang

^cDivision of Chemical and Life Sciences & Engineering, and Catalysis Center, King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia

,

Bin Dai

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China eMail: duguangfen@shzu.edu.cn

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Abstract

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Abstract

N-Heterocyclic carbene (NHC)-catalyzed vinylogous Mukaiyama aldol reaction of ketones was developed. Under the catalysis of 5 mol% NHC, α-keto esters and α-trifluoromethyl ketones reacted with 2-(trimethysilyloxy)furan efficiently to produce γ-substituted butenolides containing adjacent quaternary and tertiary carbon centers in high yields with good diastereoselectivities.

Key words

N-heterocyclic carbene - NHC - vinylogous Mukaiyama aldol reaction - 2-(trimethysilyloxy)furan - butenolide

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Referenzen

References

For recent reviews on natural products containing butenolides, see:

1a Bermejo A, Figadère B, Zafra-Polo M, Barrachina I, Estornell E, Cortes D. Nat. Prod. Rep. 2005; 22: 269
1b Sellars JD, Steel PG. Eur. J. Org. Chem. 2007; 3815
1c Prassas I, Diamandis EP. Nat. Rev. Drug Discovery 2008; 7: 926
1d Roethle PA, Trauner D. Nat. Prod. Rep. 2008; 25: 298
1e Kitson RR. A, Millemaggi A, Taylor RJ. K. Angew. Chem. Int. Ed. 2009; 48: 9426

For reviews on the synthesis of butenolides, see:

2a Negishi E, Kotora M. Tetrahedron 1997; 53: 6707
2b Montagnon T, Tofi M, Vassilikogiannakis G. Acc. Chem. Res. 2008; 41: 1001
2c Jusseau X, Chabaud L, Guillou C. Tetrahedron 2014; 70: 2595

For recent reviews on vinylogous Mukaiyama aldol reactions, see:

3a Casiraghi G, Zanardi F, Appendino G, Rassu G. Chem. Rev. 2000; 100: 1929
3b Denmark SE, Heemstra JR. Jr, Beutner GL. Angew. Chem. Int. Ed. 2005; 44: 4682
3c Kalesse M. Top. Curr. Chem. 2005; 244: 43
3d Hosokawa S, Tatsuta K. Mini-Rev. Org. Chem. 2008; 5: 1
3e Casiraghi G, Battistini L, Curti C, Rassu G, Zanardi F. Chem. Rev. 2011; 111: 3076

For recent examples of vinylogous aldol reactions of 2-(trimethylsilyloxy)furan, see:

4a Ollevier T, Bouchard JE, Desyroy V. J. Org. Chem. 2008; 73: 331
4b Yadav JS, Subba Reddy BV, Narasimhulu G, Satheesh G. Tetrahedron Lett. 2008; 49: 5683
4c Szlosek M, Figadère B. Angew. Chem. Int. Ed. 2009; 48: 1799
4d Raders SM, Verkade JG. J. Org. Chem. 2009; 74: 5417
4e Ube H, Shimada N, Terada M. Angew. Chem. Int. Ed. 2010; 49: 1858
4f Zhu N, Ma BC, Zhang Y, Wang W. Adv. Synth. Catal. 2010; 352: 1291
4g Woyciechowska M, Forcher G, Budaa S, Mlynarski J. Chem. Commun. 2012; 48: 11029
4h Nagao H, Yamane Y, Mukaiyama T. Chem. Lett. 2007; 36: 8
4i Onitsuka S, Matsuoka Y, Irie R, Katsuki T. Chem. Lett. 2003; 32: 974
4j López CS, Álvarez R, Vaz B, Faza ON, de Lera AR. J. Org. Chem. 2005; 70: 3654
4k Singh RP, Foxman BM, Deng L. J. Am. Chem. Soc. 2010; 132: 9558

5a Evans DA, Burgey CS, Kozlowski MC, Tregay SW. J. Am. Chem. Soc. 1999; 121: 686
5b Evans DA, Kozlowski MC, Murry JA, Burgey CS, Campos KR, Connell BT, Staples RJ. J. Am. Chem. Soc. 1999; 121: 669

6a Frings M, Atodiresei I, Wang YT, Runsink J, Raabe G, Bolm C. Chem. Eur. J. 2010; 16: 4577
6b Frings M, Atodiresei I, Runsink J, Raabe G, Bolm C. Chem. Eur. J. 2009; 15: 1566
6c Fabra MJ, Fraile JM, Herrerías CI, Lahoz FJ, Mayoral JA, Pérez I. Chem. Commun. 2008; 5402
6d Yu J, Zhao X, Miao Z, Chen R. Org. Biomol. Chem. 2011; 9: 6721
6e Hou G, Yu J, Yu C, Wu G, Miao Z. Adv. Synth. Catal. 2013; 355: 589

7 Meshrama HM, Ramesh P, Reddy BC, Sridhar B, Yadav JS. Tetrahedron 2011; 67: 3150
8 Chintareddy VR, Wadhwa K, Verkade JG. J. Org. Chem. 2009; 74: 8118

For recent reviews on NHC catalysis, see:

9a Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
9b Biju AT, Kuhl N, Glorius F. Acc. Chem. Res. 2011; 44: 1182
9c Mahatthananchai J, Bode JW. Chem. Sci. 2012; 3: 192
9d Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
9e Hopkinson N, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485
9f Menon RS, Biju AT, Nair V. Chem. Soc. Rev. 2015; 44: 5040
9g Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem. Rev. 2015; 115: 9307
9h Douglas J, Churchill G, Smith AD. Synthesis 2012; 44: 2295
9i Ryan SJ, Candish L, Lupton DW. Chem. Rev. 2013; 42: 4906
9j Izquierdo J, Hutson GE, Cohen DT, Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 11686

For reviews, see:

10a Fuchter MJ. Chem. Eur. J. 2010; 16: 12286
10b He L, Guo H, Wang Y, Du G.-F, Dai B. Tetrahedron Lett. 2015; 56: 972

11a Song JJ, Gallou F, Reeves JT, Tan Z, Yee NK, Senanayake CH. J. Org. Chem. 2006; 71: 1273
11b Fukuda Y, Maeda Y, Ishii S, Kondo K, Aoyama T. Synthesis 2006; 589
11c Tan M, Zhang Y, Ying JY. Adv. Synth. Catal. 2009; 351: 1390

12 Song JJ, Tan Z, Reeves JT, Gallou F, Yee NK, Senanayake CH. Org. Lett. 2005; 7: 2193
13 Wu J, Sun X, Ye S, Sun W. Tetrahedron Lett. 2006; 47: 4813

14a Raynaud J, Ciolino A, Baceiredo A, Destarac M, Bonnette F, Kato T, Gnanou Y, Taton D. Angew. Chem. Int. Ed. 2008; 47: 5390
14b Raynaud J, Liu N, Gnanou Y, Taton D. Macromolecules 2010; 43: 8853
14c Raynaud J, Liu N, Févre M, Gnanou Y, Taton D. Polym. Chem. 2011; 2: 1706
14d Lohmeijer BG, Dubois G, Leibfarth F, Pratt RC, Nederberg F, Nelson A, Waymouth RM, Wade C, Hedrick JL. Org. Lett. 2006; 8: 4683
14e Brown HA, Chang YA, Waymouth RM. J. Am. Chem. Soc. 2013; 135: 18738

For selected examples, see:

15a Zou XL, Du GF, Sun WF, He L, Ma XW, Gu CZ, Dai B. Tetrahedron 2013; 69: 607
15b Fan YC, Du GF, Sun WF, Kang W, He L. Tetrahedron Lett. 2012; 53: 2231
15c Du G.-F, Xing F, Gu C.-Z, Dai B, He L. RSC Adv. 2015; 5: 35513
15d Blanc R, Commeiras L, Parrain JL. Adv. Synth. Catal. 2010; 352: 661
15e Du G.-F, Zou X.-L, Dai B, He L. J. Saudi Chem. Soc. 2014; 18 in press; DOI: 10.1016/j.jscs.2013.12.007
15f Riduan SN, Zhang Y, Ying JY. Angew. Chem. Int. Ed. 2009; 48: 3322
15g Jacquet O, Das Neves Gomes C, Ephritikhine M, Cantat T. J. Am. Chem. Soc. 2012; 134: 2934

16a Du GF, He L, Gu CZ, Dai B. Synlett 2010; 2513
16b Cai ZH, Du GF, He L, Gu CZ, Dai B. Synthesis 2011; 2073
16c Song JJ, Tan Z, Reeves JT, Yee NK, Senanayake CH. Org. Lett. 2007; 9: 1013

17 Arduengo AJ. III, Krafczyk R, Schmutzler R. Tetrahedron 1999; 55: 14523
18 Brimble MA, Brimble MT, Gibson JJ. J. Chem. Soc., Perkin Trans. 1 1989; 179
19 Kerr MS, de Alaniz JR, Rovis T. J. Org. Chem. 2005; 70: 5725
20 Luo J, Wang H, Han X, Xu L.-W, Kwiatkowski J, Huang K.-W, Lu Y. Angew. Chem. Int. Ed. 2011; 50: 1861

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