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Enantioselective Palladium(0)‐Catalyzed Nazarov‐Type Cyclization
Author(s) -
Kitamura Kei,
Shimada Naoyuki,
Stewart Craig,
Atesin Abdurrahman C.,
Ateşin Tülay A.,
Tius Marcus A.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500881
Subject(s) - stereocenter , phosphoramidite , enantioselective synthesis , chemistry , palladium , diastereomer , catalysis , yield (engineering) , aryl , ligand (biochemistry) , pyridine , ring (chemistry) , combinatorial chemistry , medicinal chemistry , organic chemistry , dna , biochemistry , materials science , alkyl , receptor , oligonucleotide , metallurgy
A Pd 0 ‐catalyzed asymmetric Nazarov‐type cyclization is described. The optimized ligand for the reaction incorporates a weakly coordinating pyridine ring into a TADDOL‐derived phosphoramidite (TADDOL=α,α,α,α‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol). The reaction leads to the formation of cyclopentenones as single diastereoisomers that incorporate two contiguous asymmetric centers, one tertiary and one an all‐carbon‐atom quaternary stereocenter, in high yield and optical purity. It is noteworthy that the reaction does not require that substrates should be activated by aryl substituents.