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Pd/Cu Dual‐Catalyzed Asymmetric Synthesis of Highly Functional All‐Carbon Quaternary Stereocenters from Vinyl Carbonates
Author(s) -
Xue Sijing,
Lücht Alexander,
BenetBuchholz Jordi,
Kleij Arjan W.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100677
Subject(s) - stereocenter , umpolung , nucleophile , electrophile , catalysis , chemistry , enantioselective synthesis , coupling reaction , combinatorial chemistry , yield (engineering) , organic chemistry , materials science , metallurgy
Abstract The challenging metal‐catalyzed asymmetric synthesis of highly functional quaternary carbon centers using decarboxylative C(sp 3 )−C(sp 3 ) bond formation reactions is reported. The key substrate, a vinyl cyclic carbonate, is activated to provide concomitantly both the requisite nucleophile (by formal umpolung) and electrophile reaction partner preceding the asymmetric cross‐coupling process. A wide screening of reaction conditions, additives and catalyst precursors afforded a protocol that gave access to a series of compounds featuring densely functionalized, elusive quaternary carbon stereocenters in appreciable yield and with enantiomeric ratios ( er 's) of up to 90 : 10.