135514-05-5Relevant articles and documents
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)
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.
Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center
De Fusco, Claudia,Fuoco, Tiziana,Croce, Gianluca,Lattanzi, Alessandra
supporting information; experimental part, p. 4078 - 4081 (2012/09/21)
A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.
Preparation and Selected Reactions of t-Butyl 2-Methylene-3-oxoalkanoates
Hoffmann, H. Martin R.,Gassner, Andreas,Eggert, Ulrike
, p. 2475 - 2480 (2007/10/02)
The title class of 1,1-diactivated ethylenes has been prepared in two steps from aldehydes and t-butyl acrylate by (i) DABCO-catalyzed coupling to give t-butyl 2-(hydroxyalkyl)-2-propenoates 11 and (ii) low-temperature Jones oxidation, followed by swift work up at low temperature.The resulting butyl 2-methylene-3-oxoalkanoates 12 are stabilized by sterically demanding and also by aromatic groups R.For primary unhindered alkyl groups, stability is low.The compounds enter into Michael reactions, hetero Diels-Alder additions with enol ethers, and self-dimerization.Key Words: Ethylenes, 2,2-diactivated/ Michael acceptors/ 1-Oxa-1,3-butadienes/Hetero Diels-Alder reaction
