1252614-16-6Relevant articles and documents
Squaramide-Sulfonamide Organocatalyst for Asymmetric Direct Vinylogous Aldol Reactions
Sakai, Takaaki,Hirashima, Shin-ichi,Yamashita, Yoshifumi,Arai, Ryoga,Nakashima, Kosuke,Yoshida, Akihiro,Koseki, Yuji,Miura, Tsuyoshi
, p. 4661 - 4667 (2017)
Asymmetric direct vinylogous aldol reactions of furan-2(5H)-one with aldehydes in the presence of a catalytic amount of novel squaramide-sulfonamide organocatalyst resulted in the corresponding addition products with high to excellent enantioselectivities. This is the first successful report illustrating an example of highly stereoselective reactions using a squaramide-sulfonamide organocatalyst.
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.