The synthesis of trisubstituted tetrahydrofurans via the use of an organoselenium-mediated cyclisation reaction
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 303-307
- https://doi.org/10.1039/p19860000303
Abstract
The dianion derived from methyl acetoacetate may be alkylated selectively on the γ-carbon atom to form a 1,2-addition product (1) with acrolein. This material after protection as its dimethyl-t-butylsilyl derivative (2) can be cyclised with N-phenylselenophthalimide (NPSP) in the presence of various catalysts to afford dihydrofuran derivatives which are useful precursors for hydroxy-containing trisubstituted tetrahydrofurans. The X-ray crystal structure of methyl cis-4-dimethyl-t-butylsilyloxy-5- phenylselenomethyltetrahydrofuran-2-ylideneacetate, compound (4), have also been determined.This publication has 1 reference indexed in Scilit:
- Synthesis of (±)-cis-6-methyltetrahydropyran-2-ylacetic acid, a natural product from Viverra civetta, using organoselenium-mediated cyclisation reactionsJournal of the Chemical Society, Perkin Transactions 1, 1984