Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of gamma- and delta-lactones

E Yoneda; T Kaneko; SW Zhang; K Onitsuka; S Takahashi

doi:10.1021/ol990377d

Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of gamma- and delta-lactones

Org Lett. 2000 Feb 24;2(4):441-3. doi: 10.1021/ol990377d.

Authors

E Yoneda¹, T Kaneko, SW Zhang, K Onitsuka, S Takahashi

Affiliation

¹ The Institute of Scientific and Industrial Research, Osaka University, Ibaraki, Japan.

PMID: 10814346
DOI: 10.1021/ol990377d

Abstract

[reaction: see text] Ruthenium complex-catalyzed carbonylation of allenyl alcohols quantitatively gave cyclic carbonyl compounds, gamma- and delta-lactones, in which the hydroxy group of allenyl alcohols participated in the cyclization. A wide variety of allenyl alcohols, such as mono-, di-, and trisubstituted alcohols, can be used in this reaction to produce 3- and 4-substituted gamma-lactones. Similarly, the cyclic carbonylation of 3,4-pentadien-1-ol 10a and 2-methyl-4,5-hexadien-2-ol 11a gave delta-lactones, 5,6-dihydro-3-methyl-2H-pyran-2-one 10b, and 5,6-dihydro-6,6-dimethyl-3-methyl-2H-pyran. 2-one 11b, respectively, in a quantitative yield.