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Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters
Ist Teil von
Angewandte Chemie (International ed.), 2015-11, Vol.54 (46), p.13711-13714
Auflage
International ed. in English
Ort / Verlag
Weinheim: WILEY-VCH Verlag
Erscheinungsjahr
2015
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Described herein is a general and mild catalytic asymmetric 1,6‐conjugate addition of para‐quinone methides (p‐QMs), a class of challenging reactions with previous limited success. Benefiting from chiral Brønsted acid catalysis, which allows in situ formation of p‐QMs, our reaction expands the scope to general p‐QMs with various substitution patterns. It also enables efficient intermolecular formation of all‐carbon quaternary stereocenters with high enantioselectivity.
Remote control: A new catalytic asymmetric 1,6‐conjugate addition reaction of para‐quinone methides is disclosed. It is a new addition to the small family of asymmetric reaction of p‐QMs. With chiral Brønsted acid catalysis, remarkable remote stereocontrol can be achieved for a range of in situ formed p‐QMs to form all‐carbon quaternary stereocenters with high efficiency and enantioselectivity.