Enantioselective palladium(0)-catalyzed Nazarov-type cyclization

Authors

Kei Kitamura
Naoyuki Shimada
Craig Stewart
Abdurrahman Atesin, The University of Texas Rio Grande Valley
Tülay A. Ateşin, The University of Texas Rio Grande Valley
Marcus A. Tius

Document Type

Article

Publication Date

4-2015

Abstract

A Pd0-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.

Comments

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

https://onlinelibrary.wiley.com/share/7F23YKAD3NJ2MJ2AFSDE?target=10.1002/anie.201500881

Recommended Citation

Kitamura, Kei, Naoyuki Shimada, Craig Stewart, Abdurrahman C. Atesin, Tülay A. Ateşin, and Marcus A. Tius. "Enantioselective Palladium (0)‐Catalyzed Nazarov‐Type Cyclization." Angewandte Chemie International Edition 54, no. 21 (2015): 6288-6291.

Publication Title

Angewandte Chemie International Edition

DOI

https://doi.org/10.1002/anie.201500881