Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 3, Pages 1287-1297Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02816
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Funding
- National Key R&D Program of China [2016YFA0202900]
- National Natural Science Foundation of China [21572256, 21372244, 21421091]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
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Gold(I) complexes bearing sterically demanding phosphine ligands such as (t)BuXphos catalyze the cascade Rautenstrauch rearrangement/[4 + 3] cycloaddition of 1-ethynyl-2-propenyl esters. The reaction provides an efficient and straightforward route to bicyclo[3.2.1]octa-3,6-dienes with high regio- and stereoselectivity. The formation of the [4 + 3] cycloadducts likely proceeds through the cycloaddition, of a gold(I) carbenoid/gold-stabilized allyl cation intermediate with cyclopentadiene arising from Rautenstrauch rearrangement.
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