82111-78-2Relevant articles and documents
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
Catalyst-Free Conjugate Addition of Indolizines to in Situ-Generated Oxidized Morita-Baylis-Hillman Adducts
Coelho, Fernando,Silva, Thiago S.,Zeoly, Lucas A.
, p. 5438 - 5448 (2020/05/19)
Sequential one-pot 2-iodoxybenzoic acid (IBX) oxidation of Morita-Baylis-Hillman (MBH) adducts followed by catalyst-free indolizine conjugate addition was developed. The wide scopes of MBH adducts and indolizines were investigated, and densely functionalized adducts were obtained in yields of up to 94%. The conjugate addition step occurred in less than a minute at room temperature with total regioselectivity toward indolizine C3 carbon. Less nucleophilic C1 carbon was also alkylated when C3-substituted indolizines were employed as the substrate.
Hypervalent iodine catalysis for selective oxidation of Baylis-Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone
Bikshapathi, Raktani,Prathima, Parvathaneni Sai,Rao, Vaidya Jayathirtha
supporting information, p. 10300 - 10304 (2016/12/07)
An efficient, environmentally benign, eco-friendly protocol for selective oxidation of primary and secondary Baylis-Hillman alcohols to the corresponding carbonyl compounds has been developed. We have demonstrated the catalytic use of o-iodoxybenzoic acid