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Catalytic Enantioselective Nazarov Cyclization
Author(s) -
Jolit Anais,
Dickinson Cody F.,
Kitamura Kei,
Walleser Patrick M.,
Yap Glenn P. A.,
Tius Marcus A.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701117
Subject(s) - vicinal , chemistry , enantioselective synthesis , cyclopentenone , catalysis , organocatalysis , brønsted–lowry acid–base theory , quaternary carbon , organic chemistry , aryl , combinatorial chemistry , stereochemistry , alkyl
A detailed account of an asymmetric Nazarov cyclization that leads to α‐hydroxycyclopentenones bearing either vicinal, all‐carbon quaternary centers, or vicinal quaternary and tertiary centers is given. The all‐aliphatic examples represent the greatest challenge, as the dienone starting materials are not activated toward cyclization by an aryl group. The rational design and optimization of the substrates in parallel with optimization of the chiral Brønsted acid catalyst is also described, as well as a series of diastereoselective transformations of a fully substituted cyclopentenone product.