Abstract
β-Methoxycarbonyl-γ-butyrolactones bearing a γ-aromatic substituent were prepared via copper-catalyzed reductive aldol addition/lactonization domino reactions of ketones with α,β-unsaturated dicarboxylate esters and a silane under ambient temperature. The reaction has advantage of using readily available reagents, mild conditions and high efficiency.
Similar content being viewed by others
References
Bausch CC, Johnson JS (2008) Conjugate addition/Ireland–Claisen rearrangements of allyl fumarates: simple access to terminally differentiated succinates. J Org Chem 73(4):1575–1577. doi:10.1021/jo701778k
Bazin S, Feray L, Vanthuyne N, Siri D, Bertrand MP (2007) Alpha, beta-unsaturated diesters: radical acceptors in dialkylzinc-mediated tandem radical addition/aldol condensation. A straightforward synthesis of rac-nephrosteranic acid. Tetrahedron 63(1):77–85. doi:10.1016/j.tet.2006.10.049
Becker D, Kazmaier U (2013) Synthesis of tubuphenylalanines via Ireland–Claisen rearrangement. J Org Chem 78(1):59–65. doi:10.1021/jo301693d
Blanc D, Madec J, Popowyck F, Ayad T, Phansavath P, Ratovelomanana-Vidal V, Genet J-P (2007) General enantioselective synthesis of butyrolactone natural products via ruthenium-SYNPHOS (R)-catalyzed hydrogenation reactions. Adv Synth Catal 349(6):943–950. doi:10.1002/adsc.200600504
Chiu P, Leung SK (2004) Stoichiometric and catalytic reductive aldol cyclizations of alkynediones induced by Stryker’s reagent. Chem Commun 20:2308–2309. doi:10.1039/b407842j
Deschamp J, Chuzel O, Hannedouche J, Riant O (2006) Highly diastereo- and enantioselective copper-catalyzed domino reduction/aldol reaction of ketones with methyl acrylate. Angew Chem Int Ed 45(8):1292–1297. doi:10.1002/anie.200503791
Goodman CG, Walker MM, Johnson JS (2015) Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation. J Am Chem Soc 137(1):122–125. doi:10.1021/ja511701j
Hajra S, Karmakar A, Giri AK, Hazra S (2008) Concise syntheses of (+)- and (−)-methylenolactocins and phaseolinic acids. Tetrahedron Lett 49(22):3625–3627. doi:10.1016/j.tetlet.2008.04.001
Jongkol R, Choommongkol R, Tarnchompoo B, Nimmanpipug P, Meepowpan P (2009) Syntheses of methylenolactocin and nephrosterinic acid via diastereoselective acylation and chemoselective reduction-lactonization. Tetrahedron 65(32):6382–6389. doi:10.1016/j.tet.2009.06.016
Krabbe SW, Johnson JS (2015) Asymmetric total syntheses of megacerotonic acid and shimobashiric acid A. Org Lett 17(5):1188–1191. doi:10.1021/acs.orglett.5b00140
Kraft P, Denizot N (2013) Synthesis of a spirocyclic seco structure of the principal vetiver odorant khusimone. Eur J Org Chem 1:49–58. doi:10.1002/ejoc.201201318
Le Floch C, Bughin C, Le Gall E, Leonel E, Martens T (2009) Three-component synthesis of functionalized five-membered ring lactones under Barbier-like conditions. Tetrahedron Lett 50(39):5456–5458. doi:10.1016/j.tetlet.2009.07.038
Le Floch C, Le Gall E, Leonel E, Martens T, Cresteil T (2011) Synthesis and cytotoxic evaluation of novel paraconic acid analogs. Bioorg Med Chem Lett 21(23):7054–7058. doi:10.1016/j.bmcl.2011.09.092
Li Y-X, Sheng Y-L, Zhang B-S (2013a) A novel Ireland-Claisen rearrangement/Diels–Alder tandem reaction of propargylic acrylates with acyclic dienophiles. Chin Chem Lett 24(2):137–139. doi:10.1016/j.cclet.2013.01.004
Li Z, Jiang L, Li Z, Chen H (2013b) Copper hydride-catalyzed conjugate reduction-aldol addition domino Reaction of α, β-unsaturated carboxylates with ketones. Chin J Chem 31(4):539–544. doi:10.1002/cjoc.201300036
Li Z, Zhang Z, Yuan L, Jiang L, Li Z, Li Z (2014) Copper hydride catalyzed reductive aldol addition/lactonization domino reactions of α, β-unsaturated diesters. Synlett 25(5):724–728. doi:10.1055/s-0033-1340673
Li Z, Wang C, Li Z (2015) Copper-catalyzed cascade reactions of alpha, beta-unsaturated esters with keto esters. Beilstein J Org Chem 11:213–218. doi:10.3762/bjoc.11.23
Lipshutz BH, Chrisman W, Noson K, Papa P, Sclafani JA, Vivian RW, Keith JM (2000) Copper hydride-catalyzed tandem 1,4-reduction/alkylation reactions. Tetrahedron 56(18):2779–2788. doi:10.1016/s0040-4020(00)00132-0
Rodrigues SMM, Nardini V, Constantino MG, Silva GVJ (2012) Cerium metal-mediated Reformatsky-type reaction with ethyl bromosuccinate for the synthesis of novel paraconic acid analogs. Tetrahedron Lett 53(45):6136–6137. doi:10.1016/j.tetlet.2012.08.155
Shono T, Hamaguchi H, Nishiguchi I, Sasaki M, Miyamoto T, Miyamoto M, Fujita S (1981) New zinc promoted synthetic reaction of gamma-butyrolactone derivatives. Chem Lett 9:1217–1220. doi:10.1246/cl.1981.1217
Welle A, Diez-Gonzalez S, Tinant B, Nolan SP, Riant O (2006) A three-component tandem reductive aldol reaction catalyzed by N-heterocyclic carbene-copper complexes. Org Lett 8(26):6059–6062. doi:10.1021/ol062495o
Zhang ZG, Lu XY (1996) Total synthesis of phaseolinic acid by enyne cyclization. Tetrahedron Asymmetry 7(7):1923–1928. doi:10.1016/0957-4166(96)00231-5
Zhang Y, Hu X, Li S, Liao Y, Yuan W, Zhang X (2014) Organocatalytic enantioselective tandem Michael addition-oxidation of 3-substituted oxindoles with 1,4-benzoquinone. Tetrahedron 70(11):2020–2026. doi:10.1016/j.tet.2014.01.067
Zhao D, Oisaki K, Kanai M, Shibasaki M (2006) Catalytic enantioselective intermolecular reductive aldol reaction to ketones. Tetrahedron Lett 47(9):1403–1407. doi:10.1016/j.tetlet.2005.12.097
Acknowledgements
Funding was provided by Natural Science Foundation of Liaoning Province (CN) (Grant No: 2015020678).
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Li, R., Li, Z., Jiang, L. et al. An efficient synthesis of β-methoxycarbonyl-γ-butyrolactones. Chem. Pap. 71, 1825–1828 (2017). https://doi.org/10.1007/s11696-017-0175-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-017-0175-y