Cyclopentanoids from phenol. Part 4. 3-Substituted 4-hydroxycyclopent-2-enones
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 593-598
- https://doi.org/10.1039/p19810000593
Abstract
Various 3-halogeno- and 3,5,5-trihalogeno-4-hydroxycyclopent-2-enone derivatives were prepared from 3,5,5-trichloro-4-hydroxycyclopent-2-enone (2), which is available in two steps from phenol via(1R*,4R*)-3,5,5-trichloro-1,4-dihydroxycyclopent-2-ene-1-carboxylic acid (1). Conjugate addition–elimination reactions of the 3-chloro-4-(dimethy-t-butylsilyloxy)-, the 3-chloro-4-tetrahydropyranyloxy-, and the 5,5-dichloro-3-iodo-4-tetrahydropyranyloxycyclopent-2-enones (20), (21), and (7), respectively, with lithium and magnesium cuprate reagents lead to synthetically useful 3-alkyl-4-hydroxycyclopent-2-enones in high yield.Keywords
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