Trifunctionalized Allenes. Part IV. Cyclization Reactions of 4-Phosphorylated 5-Hydroxyhexa-2,3-dienoates

Author(s): Ismail E. Ismailov, Ivaylo K. Ivanov, Valerij Ch. Christov*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 9 , 2020


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Abstract:

This manuscript focuses on the reactions of 4-phosphorylated 5-hydroxyhexa-2,3-dienoates with protected or unprotected hydroxy groups involving 5-endo-trig cyclizations. Reactions with electrophiles result in mixtures of the 2,5-dihydro-1,2-oxaphosphole-5-carboxylates and the 5-phosphorylfuran- 2(5H)-ones by competitive electrophilic cyclization due to the neighboring phosphonate (phosphine oxide) and the carboxylate groups participation. 4-Phosphorylated 5-hydroxyhexa-2,3-dienoates were smoothly transformed into the corresponding 4-phosphoryl-2,5-dihydrofuran-2-carboxylates by using 5 mol % of a silver salt as a catalyst in the 5-endo-trig cycloisomerization reaction.

Keywords: 4-phosphorylated 5-hydroxyhexa-2, 3-dienoates, electrophilic cyclization, 2, 5-dihydro-1, 2-oxaphospholes, furan- 2(5H)-ones, silver-catalyzed cycloisomerization, 2, 5-dihydrofurans.

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VOLUME: 17
ISSUE: 9
Year: 2020
Published on: 16 September, 2020
Page: [726 - 733]
Pages: 8
DOI: 10.2174/1570178617666200225104238
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