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Synthesis 2017; 49(02): 293-298
DOI: 10.1055/s-0036-1588349
DOI: 10.1055/s-0036-1588349
paper
N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation
Weitere Informationen
Publikationsverlauf
Received: 14. Oktober 2016
Accepted: 20. Oktober 2016
Publikationsdatum:
18. November 2016 (online)
Dedicated to Professor Dieter Enders, a pioneer in NHC catalysis, on the occasion of his 70th birthday.
Abstract
A chiral NHC/Brønsted acid cooperative catalysis system has been developed for the asymmetric annulation of functionalized benzaldehydes and activated ketones, through dearomative generation of dienolate, to give 3-aryl-3-(perfluoroalkyl)isochroman-1-ones.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588349.
- Supporting Information
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References
-
1 Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem. Rev. 2015; 115: 9307
- 2a Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633
- 2b Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745
- 2c Du Z, Shao Z. Chem. Soc. Rev. 2013; 42: 1337
- 2d Chen D.-F, Han Z.-Y, Zhou X.-L, Gong L.-Z. Acc. Chem. Res. 2014; 47: 2365
- 3a Lathrop SP, Rovis T. J. Am. Chem. Soc. 2009; 131: 13628
- 3b Ozboya KE, Rovis T. Chem. Sci. 2011; 2: 1835
- 3c Jacobsen CB, Jensen KL, Udmark J, Jørgensen KA. Org. Lett. 2011; 13: 4790
- 4a Filloux CM, Lathrop SP, Rovis T. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20666
- 4b Padmanaban M, Biju AT, Glorius F. Org. Lett. 2011; 13: 5624
-
4c Izquierdo J, Orue A, Scheidt KA. J. Am. Chem. Soc. 2013; 135: 10634
- 4d Kuwano S, Harada S, Kang B, Oriez R, Yamaoka Y, Takasu K, Yamada K. J. Am. Chem. Soc. 2013; 135: 11485
- 4e Youn SW, Song HS, Park JH. Org. Lett. 2014; 16: 1028
- 4f Reddi Y, Sunoj RB. ACS Catal. 2015; 5: 1956
- 5 Zhao X, DiRocco DA, Rovis T. J. Am. Chem. Soc. 2011; 133: 12466
- 6a Liu G, Wilkerson PD, Toth CA, Xu H. Org. Lett. 2012; 14: 858
- 6b Fu Z, Sun H, Chen S, Tiwari B, Li G, Chi YR. Chem. Commun. 2013; 49: 261
- 6c Li J.-L, Sahoo B, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2014; 53: 10515
- 6d Xu J, Chen X, Wang M, Zheng P, Song B.-A, Chi YR. Angew. Chem. Int. Ed. 2015; 54: 5161
- 6e Pareek M, Sunoj RB. ACS Catal. 2016; 6: 3118
- 6f Wang Y, Tang M, Wang Y, Wei D. J. Org. Chem. 2016; 81: 5370
-
7 For a combination of carbene with two distinct organocatalysts, see: Wang MH, Cohen DT, Schwamb B, Mishra RK, Scheidt KA. J. Am. Chem. Soc. 2015; 137: 5891
- 8 For a review on carbene/Lewis acid catalysis, see: Cohen DT, Scheidt KA. Chem. Sci. 2012; 3: 53
-
9a DiRocco DA, Rovis T. J. Am. Chem. Soc. 2012; 134: 8094
- 9b Namitharan K, Zhu T, Chen J, Zheng P, Li X, Yang S, Song B.-A, Chi YR. Nat. Commun. 2014; 5: 3982
- 9c Liu K, Hovey MT, Scheidt KA. Chem. Sci. 2014; 5: 4026
- 9d Guo C, Fleige M, Janssen-Müller D, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2016; 138: 7840
-
10a Shen L.-T, Shao P.-L, Ye S. Adv. Synth. Catal. 2011; 353: 1943
- 10b Chen X.-Y, Xia F, Cheng J.-T, Ye S. Angew. Chem. Int. Ed. 2013; 52: 10644
- 10c Cheng J.-T, Chen X.-Y, Gao ZH, Ye S. Eur. J. Org. Chem. 2015; 1047
- 10d Jia W.-Q, Zhang H.-M, Zhang C.-L, Gao Z.-H, Ye S. Org. Chem. Front. 2016; 3: 77
-
11a Mo J, Chen X, Chi YR. J. Am. Chem. Soc. 2012; 134: 8810
-
11b Xu J, Jin Z, Chi YR. Org. Lett. 2013; 15: 5028
- 11c Wang M, Huang Z, Xu J, Chi YR. J. Am. Chem. Soc. 2014; 136: 1214
-
11d Li B.-S, Wang Y, Jin Z, Zheng P, Ganguly R, Chi YR. Nat. Commun. 2015; 6: 6207
- 12a Yao C, Xiao Z, Liu R, Li T, Jiao W, Yu C. Chem. Eur. J. 2013; 19: 456
- 12b Xiao Z, Yu C, Li T, Wang X.-S, Yao C. Org. Lett. 2014; 16: 3632
- 12c Liu R, Yu C, Xiao Z, Li T, Wang X, Xie Y, Yao C. Org. Biomol. Chem. 2014; 12: 1885
-
13 Chen X, Yang S, Song B.-A, Chi YR. Angew. Chem. Int. Ed. 2013; 52: 11134
- 14 During the course of these investigations, Glorius et al. reported a similar but racemic reaction. One example involving a chiral NHC catalyst provided product in 48% ee, see: Janssen-Müller D, Singha S, Olyschläger T, Daniliuc CG, Glorius F. Org. Lett. 2016; 18: 4444
- 15a Akiyama T. Chem. Rev. 2007; 107: 5744
- 15b Akiyama T, Mori T. Chem. Rev. 2015; 115: 9277
- 15c Terada M. Chem. Commun. 2008; 4097
- 15d Akiyama T, Itoh J, Yokota K, Fuchibe K. Angew. Chem. Int. Ed. 2004; 43: 1566
- 15e Uraguchi D, Terada M. J. Am. Chem. Soc. 2004; 126: 5356
- 16a Momiyama N, Nishimoto H, Terada M. Org. Lett. 2011; 13: 2126
- 16b Terada M, Li F, Toda Y. Angew. Chem. Int. Ed. 2014; 53: 235
- 17 Zhao X, Glover GS, Oberg KM, Dalton DM, Rovis T. Synlett 2013; 24: 1229
- 18 A concerted [4+2] cycloaddition may also be operative in this step.
- 19 Ni Q, Xiong J, Song X, Raabe G, Enders D. Synlett 2015; 26: 1465
For reviews about compatible catalysts in one system, see:
For carbene/amine catalysis, see:
For carbene/base catalysis, see:
For carbene/transition-metal catalysis, see:
For reviews, see:
For pioneering work, see: