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Synthesis 2013; 45(12): 1659-1666
DOI: 10.1055/s-0033-1338844
DOI: 10.1055/s-0033-1338844
special topic
Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Functionalized Cyclohexanes
Further Information
Publication History
Received: 28 February 2013
Accepted after revision: 03 May 2013
Publication Date:
03 June 2013 (online)
Abstract
Several reactive sites of 1,2- and 1,3-ketoamides were successively exploited in two complementary domino transformations for the synthesis of polysubstituted monocyclic or bridged bicyclic cyclohexanes, with the creation of up to six stereogenic centers. In both cases, a chiral bifunctional thiourea organocatalyst allowed efficient control of chirality in the final carbocycle.
Key words
domino reactions - ketones - amides - cyclizations - cycloalkanes - stereoselectivity - catalysis - thioureasSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are copies of 1H and 13C NMR spectra of all new compounds.
- Supporting Information
-
References
- 1a Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
- 1b Yu X, Wang W. Org. Biomol. Chem. 2008; 6: 2037
- 1c Alba A.-N, Companyo X, Viciano M, Rios R. Curr. Org. Chem. 2009; 13: 1432
- 1d Grondal C, Jeanty M, Enders D. Nature Chem. 2010; 2: 167
- 1e Pellisier H. Adv. Synth. Catal. 2012; 354: 237
- 2 Name Reactions for Carbocyclic Ring Formations . Li JJ. John Wiley; Hoboken: 2010. Chap. 4 197
- 3a Halland N, Aburel PS, Jørgensen KA. Angew. Chem. Int. Ed. 2004; 43: 1272
- 3b Zhou J, List B. J. Am. Chem. Soc. 2007; 129: 7498
- 3c Reyes E, Jiang H, Milelli A, Elsner P, Hazell RG, Jørgensen KA. Angew. Chem. Int. Ed. 2007; 46: 902
- 3d McGarraugh PG, Brenner SE. Org. Lett. 2009; 11: 5654
- 3e Hayashi Y, Okano T, Aratake S, Hazelard D. Angew. Chem. Int. Ed. 2007; 46: 4922
- 3f Anwar S, Chang H.-J, Chen K. Org. Lett. 2011; 13: 2200
- 4a Ramachary DB, Chowdari NS, Barbas III CF. Angew. Chem. Int. Ed. 2003; 42: 4233
- 4b Enders D, Hüttl MR. M, Runsik Y, Raabe G, Wendt B. Angew. Chem. Int. Ed. 2007; 46: 467
- 4c Penon O, Carlone A, Mazzanti A, Locatelli M, Sambri L, Bartoli G, Melchiorre P. Chem. Eur. J. 2008; 14: 4788
- 4d Wang Y, Han RG, Zhao YL, Yang S, Xu PF, Dixon DJ. Angew. Chem. Int. Ed. 2009; 48: 9834
- 4e Jiang K, Jia Z.-J, Yin X, Wu L, Chen Y.-C. Org. Lett. 2010; 12: 2766
- 4f Jia Y, Mao Z, Wang R. Tetrahedron: Asymmetry 2011; 22: 2018
- 5a For the concept underlying this subject, see: Bonne D, Constantieux T, Coquerel Y, Rodriguez J. Chem. Eur. J. 2013; 19: 2218
- 5b For a review, see: Bonne D, Constantieux T, Coquerel Y, Rodriguez J. Tetrahedron: Asymmetry 2010; 21: 1085
- 6a Baslé O, Raimondi W, Sanchez Duque MM, Bonne D, Constantieux T, Rodriguez J. Org. Lett. 2010; 12: 5246
- 6b Sanchez Duque MM, Baslé O, Isambert N, Gaudel-Siri A, Génisson Y, Plaquevent J.-C, Rodriguez J, Constantieux T. Org. Lett. 2011; 13: 3296
- 7a Nakamura A, Lectard S, Hashizume D, Hamashima Y, Sodeoka M. J. Am. Chem. Soc. 2010; 132: 4036
- 7b Shi D, Xie Y, Zhou H, Xia C, Huang H. Angew. Chem. Int. Ed. 2012; 51: 1248
- 7c Varga S, Jakab G, Drahos L, Holczbauer T, Czugler M, Soós T. Org. Lett. 2011; 13: 5416
- 8 Vakulya B, Varga S, Csámpai A, Soós T. Org. Lett. 2005; 7: 1967
- 9 Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y. J. Am. Chem. Soc. 2005; 127: 119
- 10 Malerich JP, Hagihara K, Rawal VH. J. Am. Chem. Soc. 2008; 130: 14416
- 11a Presset M, Coquerel Y, Rodriguez J. ChemCatChem 2012; 4: 172
- 11b Presset M, Coquerel Y, Rodriguez J. Chem. Rev. 2013; 113: 525
- 12a Boddaert T, Coquerel Y, Rodriguez J. Adv. Synth. Catal. 2009; 351: 1744
- 12b Boddaert T, Coquerel Y, Rodriguez J. Chem. Eur. J. 2011; 17: 2266
- 13 For the method used to prepare the 1,3-ketoamides, see: Presset M, Coquerel Y, Rodriguez J. J. Org. Chem. 2009; 74: 415
- 14 HPLC analysis of the corresponding hemiaminal 10d after oxidation showed that it was obtained with an er of 84:1. See ref. 6b for details.
For reviews on organocatalytic domino reactions, see:
For selected examples of two-component approaches, see:
For selected examples of multicomponent approaches, see:
For similar sequences with 1,2-keto esters and a chiral copper(II) complex, see:
For a related three-component one-pot sequence, see:
For recent reviews, see:
For examples of N-heterocyclic carbene-catalyzed enolization and Michael additions, see: