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Gold(I)‐ and Yb(OTf) 3 ‐Cocatalyzed Rearrangements of Epoxy Alkynes: Transfer of a Carbonyl Group in a Five‐Membered Carbocycle
Author(s) -
Dai LunZhi,
Shi Min
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902321
Subject(s) - intramolecular force , catalysis , domino , chemistry , indene , epoxy , cascade reaction , combinatorial chemistry , photochemistry , organic chemistry
We report here the intramolecular reactions between α,β‐epoxy ketones and alkynes cocatalyzed by gold(I) and Yb(OTf) 3 . This new catalytic system based on a combination of gold(I) and Yb(OTf) 3 allows facile transformation of epoxy alkynes to give novel indene derivatives in moderate to good yields under mild conditions. Moreover, we describe here the first observation of a transfer of a carbonyl group in a five‐membered carbocycle during gold‐catalyzed reactions. This proposed mechanism is corroborated by isotope‐labeling experiments (D and 13 C). Furthermore, the probable role of each catalyst in this interesting domino reaction has been examined by 31 P NMR experiments. The utilization of gold catalysts combined with rare‐earth metal salts offers a new concept for the design of catalyst combinations for domino or cascade reactions.