Abstract
Convenient methods for retro-aldol reactions of α, β-unsaturated ketones in micellar media under acidic or basic conditions are proposed that enable obtaining optically pure (3R)-methylcyclohexanone and (1R,4R)-4-methylmenthone in high yields.
Graphical abstract
Similar content being viewed by others
References
Nielsen AT, Houlihan WJ (1968) The aldol condensation. In: Organic reactions, vol 16. Wiley Interscience, p 1
Mukaiyama T (1982) The directed aldol reaction. In: Organic reactions, vol 28. Wiley Interscience, p 203
Djerassi C, Burakevich J, Chamberlin JW, Elad D, Toda T, Stork G (1964) J Am Chem Soc 86:465
Eisenbraun EJ, Hanel PG, Schorno KC, Dilgen FS, Osiecki J (1967) J Org Chem 32:3010
dos Santos EM, Bogdan M, Victor MM, Tenius BSM, de Oliveira ER (2007) J Braz Chem Soc 18:370
Rupe H, Kambli E (1927) Justus Liebigs Ann Chem 459:195
Johnson WS (1937) J Am Chem Soc 65:1317
Akhrem AA, Titov YA (1970) Total steroid synthesis. Plenum Press, New York
Vashchenko VV (1997) Thesis, Cand Sci (Chem), Institute for Single Crystal, Kharkov
Kutulya LA, Vashchenko VV, Kuznetsov VP, Kulishov VI, Lakin EE (1995) Kristallografiya 40:1015
Vashchenko V, Dryshlyak T, Shkolnikova N, Kutulya L (1999) Mol Cryst Liq Cryst 328:245
Quesnel Y, Toupet L, Duhamel L, Duhamel P, Poirier J-M (1999) Tetrahedron Asymmetry 10:1015
Smith MB, March J (2007) March’s advanced organic chemistry. Reactions, mechanisms and structure, 6th edn. Wiley, Hoboken, New Jersey
Evans DA (1984) Stereoselective alkylation reactions of chiral metal enolates. In: Asymmetric synthesis, vol 3. Academic Press, New York, p 1
Fieser LF, Fieser M (1959) Steroids. Reinhold Publishing Corp, New York
Tascioglu S (1996) Tetrahedron 52:11113
Ruasse M-F, Blagoeva IB, Ciri R, Garcia-Rio L, Leis JR, Marques A, Mejuto J, Monnier E (1997) Pure Appl Chem 69:1923
Buck KT, Boeing AJ, Dolfini JE, Glinka J (1987) Method of catalytically hydrolyzing α,β-unsaturated carbonyl compounds. EP 242934; (1988) Chem Abstr 108:114670x
Buck KT, Boeing AJ, Dolfini JE (1987) Method of producing benzaldehyde. US Patent 4673766; (1987) Chem Abstr 107:156970e
Vashchenko V, Kutulya L, Krivoshey A (2007) Synthesis 2125
Hassner A, Mead TC (1961) Tetrahedron 20:2201
Vashchenko VV, Pivnenko NS, Kutulya LA, Petrenko AS, Iksanova SV, Goodby JW (2000) Russ Chem Bull 49:1218
Gottlieb HE, Kotlyar V, Nudelman A (1997) J Org Chem 62:7512
Eisenbraun EJ, McElvain SM (1955) J Am Chem Soc 77:3383
Gurst JE (1992) J Chem Educ 69:774
Acknowledgments
Financial support from from the National Academy of Science of the Ukraine (project no. 0107U003550) is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Vashchenko, E.V., Knyazeva, I.V., Krivoshey, A.I. et al. Retro-aldol reactions in micellar media. Monatsh Chem 143, 1545–1549 (2012). https://doi.org/10.1007/s00706-012-0811-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-012-0811-8