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Platinum(II)‐Catalyzed Reaction of γ,δ‐Ynones with Alkenes for the Construction of 8‐Oxabicyclo[3.2.1]octane Skeletons: Generation of Platinum‐Containing Carbonyl Ylides from Acyclic Precursors
Author(s) -
Kusama Hiroyuki,
Ishida Kento,
Funami Hideaki,
Iwasawa Nobuharu
Publication year - 2008
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.200705129
Subject(s) - cycloaddition , chemistry , styrene , substituent , octane , alkyl , platinum , catalysis , bicyclic molecule , medicinal chemistry , hydrogen atom , carbene , substrate (aquarium) , organic chemistry , copolymer , polymer , oceanography , geology
Two types of bicycles can be prepared selectively by the title reaction, depending on whether or not a substituent is present at the propargylic position of the ynone substrate (see scheme). The cycloaddition of carbonyl ylides derived from γ,δ‐ynones with vinyl ethers (or styrene) gave intermediate bicyclic carbene complexes, which underwent a 1,2‐hydrogen‐atom shift or rearrangement to provide the products. R 1 =alkyl, Ph; R 3 =alkyl.