A Novel Oxy‐Oxonia(Azonia)‐<i>Cope</i> Reaction: Serendipitous Discovery and Its Application to the Synthesis of Macrocyclic Musks

Yue Zou, Lijun Zhou, Changming Ding, Quanrui Wang, Philip Kraft, Andreas Goeke

doi:10.1002/cbdv.201400058

A Novel Oxy‐Oxonia(Azonia)‐<i>Cope</i> Reaction: Serendipitous Discovery and Its Application to the Synthesis of Macrocyclic Musks

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書誌事項

公開日: 2014-10

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http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/cbdv.201400058

公開者: Wiley

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<jats:title>Abstract</jats:title><jats:p>This brief review, including new experimental results, is the summary of a talk at the GDCh conference ‘flavors & fragrances 2013’ in Leipzig, Germany, 11th–13th September, 2013. Musk odorants are indispensable in perfumery to lend sensuality to fine fragrances, a nourishing effect to cosmetics, and a comforting feeling to laundry. We have recently found serendipitously a new oxy‐oxonia‐<jats:italic>Cope</jats:italic> rearrangement. In this account, we review the background of oxonia‐sigmatropic rearrangements and the discovery of this novel reaction. Special attention is focused on the versatile lactone and lactam formation reactions <jats:italic>via</jats:italic> [<jats:italic>n</jats:italic>+4] ring enlargement and the macrocyclization in the synthesis of new macrocyclic musks. The synthesized structures provide new insights into the structureodor relationships of musks.</jats:p>