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Palladium‐Catalyzed Asymmetric Synthesis of 2‐Alkynyl Oxacycles
Author(s) -
Daniels David S. B.,
Thompson Amber L.,
Anderson Edward A.
Publication year - 2011
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.201105720
Subject(s) - palladium , catalysis , chemistry , combinatorial chemistry , organic chemistry
Oxyacetylene : Unusual palladium‐catalyzed cyclizations of cyclic and acyclic propargylic carbonates give 2‐alkynyl oxacycles. The reactions proceed with very high stereoselectivity for both syn ‐ and anti ‐disubstituted furans and pyrans, and with exceptional regioselectivity. In addition, two‐directional cyclizations of bis‐propargylic carbonate substrates yield bifurans with complete stereocontrol for all diastereomers.