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Pd II ‐ and Pt II ‐Mediated Polycyclization Reactions of 1,5‐ and 1,6‐Dienes: Evidence in Support of Carbocation Intermediates
Author(s) -
Koh Jeong Hwan,
Gagné Michel R.
Publication year - 2004
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.200453913
Subject(s) - carbocation , chemistry , yield (engineering) , pincer movement , pinacol , heteroatom , medicinal chemistry , diastereomer , stereochemistry , organic chemistry , catalysis , physics , ring (chemistry) , thermodynamics
Pincer‐ligated Pd II and Pt II dicationic complexes efficiently generate cations from 1,5‐ and 1,6‐dienes. These transient cations can be selectively trapped with heteroatoms, alkenes, and through pinacol rearrangements. For example, trienylphenol 1 is converted into tetracyclic 2 in high yield and diastereomeric ratio (see scheme).