Synthesis 2021; 53(19): 3535-3544
DOI: 10.1055/a-1493-6670
feature

Aza-Peterson Olefinations: Rapid Synthesis of (E)-Alkenes

Thomas K. Britten
,
Ashley J. Basson
,
Dean D. Roberts
,
We thank Manchester Metropolitan University (MMU) for startup funding. T.K.B. thanks MMU for Strategic Opportunities Funding. M.G.M. thanks MMU, Royal Society of Chemistry and Medical Research Council for funding.


Abstract

An aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser’s base and added to N-phenyl imines or ketones to directly give the desired products in high yields.

Supporting Information



Publikationsverlauf

Eingereicht: 31. März 2021

Angenommen nach Revision: 28. April 2021

Accepted Manuscript online:
28. April 2021

Artikel online veröffentlicht:
25. Mai 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Peterson DJ. J. Org. Chem. 1968; 33: 780
  • 2 Van Staden LF, Gravestock D, Ager DJ. Chem. Soc. Rev. 2002; 31: 195
  • 3 Chan TH, Chang E, Vinokur E. Tetrahedron Lett. 1970; 11: 1137
  • 4 Chan TH, Chang E. J. Org. Chem. 1974; 39: 3264
  • 5 Palomo C, Aizpurua JM, García JM, Ganboa I, Cossio FP, Lecea B, López C. J. Org. Chem. 1990; 55: 2498
  • 6 Werner V, Klatt T, Fujii M, Markiewicz J, Apeloig Y, Knochel P. Chem. Eur. J. 2014; 20: 8338
  • 7 Klatt T, Werner V, Maximova MG, Didier D, Apeloig Y, Knochel P. Chem. Eur. J. 2015; 21: 7830
  • 8 Das M, Manvar A, Jacolot M, Blangetti M, Jones RC, O’Shea DF. Chem. Eur. J. 2015; 21: 8737
  • 9 Manvar A, O’Shea DF. Eur. J. Org. Chem. 2015; 7259
  • 10 Das M, O’Shea DF. Org. Lett. 2016; 18: 336
  • 11 Lambert JB, Wang GT, Finzel RB, Teramura DH. J. Am. Chem. Soc. 1987; 109: 7838
  • 12 Ager DJ. J. Chem. Soc., Perkin Trans. 1 1986; 183
  • 13 Bassindale AR, Ellis RJ, Taylor PG. Tetrahedron Lett. 1984; 25: 2705
  • 14 Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
  • 15 Al-Badri H, About-Jaudet E, Collignon N. Tetrahedron Lett. 1996; 37: 2951
  • 16 Al-Badri H, About-Jaudet E, Collignon N. J. Chem. Soc., Perkin Trans. 1 1996; 931
  • 17 Lau PW. K, Chan TH. Tetrahedron Lett. 1978; 19: 2383
  • 18 Wang Y, West F. Synthesis 2002; 99
  • 19 Dong DJ, Li HH, Tian SK. J. Am. Chem. Soc. 2010; 132: 5018
  • 20 Lee RJ, Lindley MR, Pritchard GJ, Kimber MC. Chem. Commun. 2017; 53: 6327
  • 21 Mori M, Sakakibara N, Kinoshita A. J. Org. Chem. 1998; 63: 6082
  • 22 Tonogaki K, Mori M. Tetrahedron Lett. 2002; 43: 2235
  • 23 Ozawa T, Aoyagi S, Kibayashi C. J. Org. Chem. 2001; 66: 3338
  • 24 McAlpine NJ, Wang L, Carrow BP. J. Am. Chem. Soc. 2018; 140: 13634
  • 25 Nguyen VT, Dang HT, Pham HH, Nguyen VD, Flores-Hansen C, Arman HD, Larionov OV. J. Am. Chem. Soc. 2018; 140: 8434
  • 26 Liu Q, Wang ZY, Peng XS, Wong HN. C. J. Org. Chem. 2018; 83: 6325
  • 27 Carter MJ, Fleming I, Percival A. J. Chem. Soc., Perkin Trans. 1 1981; 2415
  • 28 Chan TH, Li JS. J. Chem. Soc., Chem. Commun. 1982; 969
  • 29 Corriu R, Escudie N, Guerin C. J. Organomet. Chem. 1984; 264: 207
  • 30 Borg T, Tuzina P, Somfai P. J. Org. Chem. 2011; 76: 8070
  • 31 Borg T, Timmer B, Somfai P. Tetrahedron Lett. 2013; 54: 3916
  • 32 Britten TK, McLaughlin MG. J. Org. Chem. 2020; 85: 301
  • 33 Fleming P, O’Shea DF. J. Am. Chem. Soc. 2011; 133: 1698
  • 34 Schlosser M, Franzini L. Synthesis 1998; 707
  • 35 Lochmann L, Pospíšil J, Lím D. Tetrahedron Lett. 1966; 7: 257
  • 36 Schlosser M. J. Organomet. Chem. 1967; 8: 9
  • 37 Schlosser M. Pure Appl. Chem. 1988; 60: 1627
  • 38 Deagostino A, Tivola PB, Prandi C, Venturello P. J. Chem. Soc., Perkin Trans. 1 2001; 2856
  • 39 Unkelbach C, O’Shea DF, Strohmann C. Angew. Chem. Int. Ed. 2014; 53: 553
  • 40 Szudkowska-Frątczak J, Marciniec B, Hreczycho G, Kubicki M, Pawluć P. Org. Lett. 2015; 17: 2366
  • 41 Li Z, Zhang L, Nishiura M, Luo G, Luo Y, Hou Z. J. Am. Chem. Soc. 2020; 142: 1966
  • 42 Xu J, Zhuang R, Bao L, Tang G, Zhao Y. Green Chem. 2012; 14: 2384
  • 43 Zhang E, Tian H, Xu S, Yu X, Xu Q. Org. Lett. 2013; 15: 2704
  • 44 Tan DW, Li HX, Young DJ, Lang JP. Tetrahedron 2016; 72: 4169
  • 45 Lawson JR, Wilkins LC, Melen RL. Chem. Eur. J. 2017; 23: 10997
  • 46 Garrido-Castro AF, Gini A, Maestro MC, Alemán J. Chem. Commun. 2020; 56: 3769
  • 47 Goh KK. K, Kim S, Zard SZ. J. Org. Chem. 2013; 78: 12274
  • 48 Babudri F, Farinola GM, Fiandanese V, Mazzone L, Naso F. Tetrahedron 1998; 54: 1085
  • 49 Dhara S, Diesendruck CE. Eur. J. Org. Chem. 2017; 1184
  • 50 Guastavino JF, Budén ME, Rossi RA. J. Org. Chem. 2014; 79: 9104
  • 51 Zhong JJ, Liu Q, Wu CJ, Meng QY, Gao XW, Li ZJ, Chen B, Tung CH, Wu LZ. Chem. Commun. 2016; 52: 1800
  • 52 Landge VG, Yadav V, Subaramanian M, Dangarh P, Balaraman E. Chem. Commun. 2019; 55: 6130