A facile efficient approach to the 2-styrylmalonates via the Lewis acid-catalyzed isomerization of 2-arylcyclopropane-1,1-dicarboxylates has been developed. The efficiency of this method was demonstrated for a representative series of such cyclopropanes. The isomerization proceeds chemo-, regio-and stereoselectively to afford E-styrylmalonates in good yields.
(3 + 2)-Annulation of donor-acceptor cyclopropanes to alkynes induced by both Lewis and Brønsted acids has been developed. The reaction provides a rapid approach to functionalized indenes displaying intense visible emission (λmax = 430 nm, Φ = 0.28-0.34).
Lewis Acid-Catalyzed Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates: A New Efficient Route to 2-Styrylmalonates. -The isomerizations proceed chemo-, regio-and stereoselectively to give (E)-styrylmalonates and heterocyclic analogues. Cyclopropanes bearing moderately nucleophilic aryl substituents undergo the isomerization by treatment with TmsOTf, while the reactions of cyclopropanes with highly nucleophilic aryl or heteroaryl substituents are catalyzed by Sn(OTf) 2 . -(CHAGAROVSKIY, A. O.; IVANOVA, O. A.; RAKHMANKULOV, E. R.; BUDYNINA, E. M.; TRUSHKOV, I. V.; MELNIKOV*, M. Y.; Adv. Synth. Catal. 352 (2010) 18, 3179-3184, http://dx.
Lewis and Broensted Acid Induced (3 + 2)-Annulation of Donor-Acceptor Cyclopropanes to Alkynes: Indene Assembly. -(3 + 2)-Annulation of donor--acceptor cyclopropanes to alkynes induced by both Lewis and Broensted acids is developed. The reaction provides a rapid access to functionalized indenes displaying intense visible emission ( max = 430 nm). The new method can also be applied to the synthesis of cyclopenta[b]indoles (IX). -(RAKHMANKULOV, E. R.; IVANOV, K. L.; BUDYNINA*, E. M.; IVANOVA, O. A.; CHAGAROVSKIY, A. O.; SKVORTSOV, D. A.; LATYSHEV, G. V.; TRUSHKOV, I. V.; MELNIKOV, M. Y.; Org. Lett. 17 (2015) 4, 770-773, http://dx.doi.org/10.1021/ol5037562 ; Dep. Chem., Moscow State Univ., Moscow 119991, Russia; Eng.) -B. Guendogan
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