Abstract
The results of proline-catalyzed aldol reaction of acetone with O,O′-alkylidene derivatives of glyceraldehyde are determined by the configuration of the chiral center in the aldehyde. The reaction of (S)-2,3-O-alkylideneglyceraldehyde with acetone in the presence of L-proline was characterized by higher diastereoselectivity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Berkessel, A. and Gröger, H., Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Weinheim: Wiley-VCH, 2005.
Carreira, E.M., Fettes, A., and Marti, C., Organic Reactions, Overman, L., Ed., New York: Wiley, 2006, vol. 67, p. 1.
Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, Dalko, P.I., Ed., Weinheim: Wiley-VCH, 2013, vol. 1.
Asymmetric Organocatalysis, List, B., Ed., (Topics in Current Chemistry, vol. 291), Heidelberg: Springer, 2009.
Scheffler, U. and Mahrwald, R., Chem. Eur. J., 2013, vol. 19, p. 14 346.
List, B., Tetrahedron, 2002, vol. 58, p. 5573.
Notz, W., Tanaka, F., and Barbas, A.F. III, Acc. Chem. Res., 2004, vol. 37, p. 580.
Kotsuki, H., Ikishima, H., and Okuyama, A., Heterocycles, 2008, vol. 75, p. 493.
Kotsuki, H., Ikishima, H., and Okuyama, A., Heterocycles, 2008, vol. 75, p. 757.
Panday, S.K., Tetrahedron: Asymmetry, 2011, vol. 22, p. 1817.
Sakthivel, K., Notz, W., Bui, T., and Barbas, C.F. III, J. Am. Chem. Soc., 2001, vol. 123, p. 5260.
List, B., Pojarliev, P., and Castello, C., Org. Lett., 2001, vol. 3, p. 573.
Martinez, A., Zumbansen, K., Döhring, A., van Gemmeren, M., and List, B., Synlett, 2014, vol. 25, p. 932.
Enders, D. and Grondal, C., Angew. Chem., Int. Ed., 2005, vol. 44, p. 1210.
Grondal, C. and Enders, D., Tetrahedron, 2006, vol. 62, p. 329.
Enders, D., Paleček, J., and Grondal, C., Chem. Commun., 2006, p. 655.
Grondal, C. and Enders, D., Synlett, 2006, p. 3507.
Yokoyama, H., Otaya, K., Kobayashi, H., Miyazawa, M., Yamaguchi, S., and Hirai, Y., Org. Lett., 2000, vol. 2, p. 2427.
Niu, C., Pettersson, T., and Miller, M.J., J. Org. Chem., 1996, vol. 61, p. 1014.
Michel, P. and Ley, S.V., Synthesis, 2003, p. 1598.
Woodward, A.R., Burks, H.E., Chan, L.M., and Morken, J.P., Org. Lett., 2005, vol. 7, p. 5505.
Bahmanyar, S., Houk, K.N., Martin, H.J., and List, B., J. Am. Chem. Soc., 2003, vol. 125, p. 2475.
Arnó, M. and Domingo, L.R., Theor. Chem. Acc., 2002, vol. 108, p. 232.
Rankin, K.N., Gauld, J.W., and Boyd, R.J., J. Phys. Chem. A, 2002, vol. 106, p. 5155.
Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © Yu.Yu. Kozhemyakin, Yu.Yu. Kozyrkov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 4, pp. 583–586.
Rights and permissions
About this article
Cite this article
Kozhemyakin, Y.Y., Kozyrkov, Y.Y. Proline-catalyzed aldol reaction of acetone with (R)- and (S)-2,3-O-alkylideneglyceraldehydes. Russ J Org Chem 51, 566–568 (2015). https://doi.org/10.1134/S107042801504017X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107042801504017X