96013-53-5Relevant articles and documents
Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones
Chen, Ming,Rago, Alexander J.,Dong, Guangbin
supporting information, p. 16205 - 16209 (2018/11/23)
The development of a general platinum-catalyzed desaturation of N-protected lactams, ketones, and lactones to their conjugated α,β-unsaturated counterparts is reported. The reaction operates under mildly acidic conditions at room temperature or 50 °C. It is scalable and tolerates a wide range of functional groups. The complementary reactivity to the palladium-catalyzed desaturation is demonstrated in the efficient conversion of iodide, bromide, and sulfur-containing substrates.
Catalytic, asymmetric vinylogous Mukaiyama aldol reactions of pyrrole- and furan-based dienoxy silanes: How the diene heteroatom impacts stereocontrol
Curti, Claudio,Ranieri, Beatrice,Battistini, Lucia,Rassu, Gloria,Zambrano, Vincenzo,Pelosi, Giorgio,Casiraghi, Giovanni,Zanardi, Franca
supporting information; experimental part, p. 2011 - 2022 (2010/11/17)
Denmark's chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base-Lewis acid catalyst for the vinylogous Mukaiyama aldol reaction of pyrrole- and furan-based dienoxy silanes with aromatic and heteroaromatic aldehydes. This asymmetric methodology provides a powerful synthetic entry to a variety of d-hydroxylated g-butenolide-type frameworks with high efficiency and valuable margins of regio-, diastereo-, and enantioselectivity. Notably, the nature of the heteroatom within the vinylogous dienoxy silane donor heavily impacts the diastereocontrol, with syn-configured aldol adducts emerging from pyrroles bearing electron- withdrawing N-protecting groups (Boc, Ts, and Cbz) and anti-configured adducts prevailing when furan- or N-alkyl/alkenylpyrrole donors are involved.
A new synthesis of γ-lactams based on the reaction of vinyl sulfilimines with dichloroketene
Wang, Qiu,Nara, Shinji,Padwa, Albert
, p. 839 - 841 (2007/10/03)
(Chemical Equation Presented) The reactions of several aryl-, furanyl-, and vinyl substituted sulfilimines with dichloroketene proceeded at 25°C to yield thioalkyl substituted γ-lactams which, in turn, were converted to a variety of nitrogen-containing substrates.