Selective Mono-allylation of 1,3-Diketones and Their Use in the Synthesis of 3-Allyl Chromones and Benzannulated 6,5-Bicyclic Ketals

Brooke E Swaney; Sinan Gai; Mitchell R Clark; Bill C Hawkins

doi:10.1002/asia.201801695

Selective Mono-allylation of 1,3-Diketones and Their Use in the Synthesis of 3-Allyl Chromones and Benzannulated 6,5-Bicyclic Ketals

Chem Asian J. 2019 Apr 15;14(8):1102-1105. doi: 10.1002/asia.201801695. Epub 2018 Dec 28.

Authors

Brooke E Swaney¹, Sinan Gai¹, Mitchell R Clark¹, Bill C Hawkins¹

Affiliation

¹ Department of Chemistry, University of Otago, Dunedin, 9054, New Zealand.

PMID: 30552751
DOI: 10.1002/asia.201801695

Abstract

The selective mono-allylation of 1,3-diketone containing compounds is described. The reaction proceeds under mild reaction conditions and in moderate to high yield (66-99 %). Using this procedure to access the key mono-allylated intermediate, the hitherto difficult to access 3-allyl chromones were synthesized in excellent yield (87-98 %). Finally, the utility of this newly developed procedure was showcased through the rapid synthesis of the scaffold of the xyloketal family of natural products.

Keywords: allylation; chromone; domino reactions; synthetic methodology; xyloketal.