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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 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.201500881
Subject(s) - stereocenter , phosphoramidite , catalysis , palladium , enantioselective synthesis , chemistry , diastereomer , yield (engineering) , ligand (biochemistry) , aryl , pyridine , ring (chemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , dna , biochemistry , receptor , alkyl , 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.