Premium
(3+3)‐Annulation of Carbonyl Ylides with Donor–Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis
Author(s) -
Petzold Martin,
Jones Peter G.,
Werz Daniel B.
Publication year - 2019
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.201814409
Subject(s) - annulation , chemistry , lewis acids and bases , catalysis , reactivity (psychology) , medicinal chemistry , diazo , acceptor , stereochemistry , organic chemistry , medicine , physics , alternative medicine , pathology , condensed matter physics
Abstract The first (3+3)‐annulation process of donor–acceptor cyclopropanes using synergistic catalysis is reported. The Rh 2 (OAc) 4 ‐catalyzed decomposition of diazo carbonyl compounds generated carbonyl ylides in situ. These 1,3‐dipoles were converted with donor–acceptor cyclopropanes, activated by Lewis acid catalysis, to afford multiply substituted pyran scaffolds in high yield and diastereoselectivity. Extensive optimization studies enabled access to 9‐oxabicyclo[3.3.1]nonan‐2‐one and 10‐oxabicyclo[4.3.1]decen‐2‐ol cores, exploiting solvent effects on intermediate reactivity.