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Aitken, Lewis S.; Hammond, Lisa E.; Sundaram, Rajkumar; Shankland, Kenneth; Brown, Geoffrey D.; Cobb, Andre J. A. (2015)
Publisher: The Royal Society of Chemistry
Languages: English
Types: Article
Subjects:
An organocatalytic asymmetric synthesis of a novel, highly functionalised cyclopropane system furnished with versatile substituents and containing a quaternary centre is described. The process utilises a new bifunctional catalyst based on the cinchona alkaloid framework and the products made using this catalyst were obtained as single diastereoisomers, with very high enantioselectivities (up to 96% ee). We have also demonstrated that these resulting cyclopropanes are very useful synthetic intermediates to interesting products, such as the difficult to access d3-amino acids.
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    • 1 For a review on the occurrences of cyclopropanes in nature and recent syntheses see D. Y.-K. Chen, R. H. Pouwer and J.-A. Richard, Chem. Soc. Rev., 2012, 41, 4631.
    • 2 M. A. Cavitt, L. H. Phun and S. France, Chem. Soc. Rev., 2014, 43, 804.
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    • 5 For recent discussion on this extensive area of catalysis, see (a) A. F. Trindade, J. A. S. Coelho, C. A. M. Afonso, L. F. Veiros and P. M. P. Gois, ACS Catal., 2012, 2, 370; (b) M. P. Doyle, R. Duffy, M. Ratnikov and L. Zhou, Chem. Rev., 2010, 110, 704; (c) H. M. L. Davies and J. R. Denton, Chem. Soc. Rev., 2009, 38, 3061 and references therein.
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    • 9 See reference 3 and the appropriate section of C. M. R. Volla, I. Atodiresei and M. Rueping, Chem. Rev., 2013, 114, 2390; for detailed review.
    • 10 (a) A. J. A. Cobb, in Enantioselective Organocatalyzed Reactions II: Asymmetric C-C Bond Formation Processes, ed. R. Mahrwald, Springer, Dordrecht, 2011; (b) L. S. Aitken, N. R. Arezki, A. Dell'Isola and A. J. A. Cobb, Synthesis, 2013, 2627.
    • 11 (a) S. Rajkumar, K. Shankland, J. M. Goodman and A. J. A. Cobb, Org. Lett., 2013, 15, 1386. For a related process, see (b) S. Meninno, G. Groce and A. Lattanzi, Org. Lett., 2013, 15, 3436.
    • 12 For minireviews, see: (a) M. Kotke and P. R. Schreiner, in Hydrogen Bonding in Organic Synthesis, ed. P. Pihko, Wiley-VCH, 2009, pp. 141- 351; (b) H. Miyabe and Y. Takemoto, Bull. Chem. Soc. Jpn., 2008, 81, 785-795; (c) S. J. Connon, Chem. Commun., 2008, 2499; (d) T. Marcelli, J. H. van Maarseveen and H. Hiemstra, Angew. Chem., Int. Ed., 2006, 45, 7496; Other work by us in this area includes: (e) W. J. Nodes, D. R. Nutt, A. M. Chippindale and A. J. A. Cobb, J. Am. Chem. Soc., 2009, 131, 16016; ( f ) S. Rajkumar, K. Shankland, G. D. Brown and A. J. A. Cobb, Chem. Sci., 2012, 3, 584.
    • 13 The C6-OH of cupreine has been shown to be very important in other reactions for obtaining high selectivities. See: (a) H. Li, Y. Wang, L. Tang and L. Deng, J. Am. Chem. Soc., 2004, 126, 9906; (b) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman and L. Deng, Angew. Chem., Int. Ed., 2005, 44, 105; (c) X. Liu, H. Li and L. Deng, Org. Lett., 2005, 7, 167; (d) H. Li, J. Song, X. Liu and L. Deng, J. Am. Chem. Soc., 2005, 127, 8948; (e) R. Dodda, J. J. Goldman, T. Mandal, C.-G. Zhao, G. A. Broker and E. R. T. Tiekink, Adv. Synth. Catal., 2008, 350, 537; ( f ) P. Chauhan and S. S. Chimni, Tetrahedron Lett., 2013, 54, 4613; (g) P. Chauhan and S. S. Chimni, RSC Adv., 2012, 2, 737.
    • 14 U. Das, Y.-L. Tsai and W. Lin, Org. Biomol. Chem., 2013, 11, 44.
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    • 16 The only previous report of this compound is in European Pat., EP1512678 A1, 2005, which obtained it in a 60% ee.
    • 17 For other (longer) syntheses, see (a) R. Karla, B. Ebert, C. Thorkildsen, C. Herdeis, T. N. Johansen, B. Nielsen and P. Krogsgaard-Larsen, J. Med. Chem., 1999, 42, 2053; (b) Z.-T. He, Y.-B. Wei, H.-J. Yu, C.-Y. Sun, C.-G. Feng, P. Tian and G.-Q. Lin, Tetrahedron, 2012, 68, 9186; (c) M. I. Attia, C. Herdeis and H. Br¨auner-Osborne, Molecules, 2013, 18, 10266 (non-chiral).
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