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Diastereospecific Nazarov Cyclization of Fully Substituted Dienones: Generation of Vicinal All‐Carbon‐Atom Quaternary Stereocenters
Author(s) -
Jolit Anais,
VazquezRodriguez Saleta,
Yap Glenn P. A.,
Tius Marcus A.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201305218
Subject(s) - vicinal , stereocenter , chemistry , carbon atom , carbon fibers , carbonate , atom (system on chip) , stereochemistry , combinatorial chemistry , computer science , organic chemistry , catalysis , enantioselective synthesis , operating system , alkyl , composite number , algorithm
No vacancy : Fully substituted dienones that are highly polarized by a vinylogous carbonate group were found to undergo a remarkably rapid and diastereospecific Nazarov cyclization that led to cyclopentenones with vicinal all‐carbon‐atom quaternary centers (see example; SEM=2‐(trimethylsilyl)ethoxymethyl, Tf=trifluoromethanesulfonyl).