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Highly stereloselective synthesis of 2,5-disubstituted 3-vinylidene tetetrahydrofurans via Prins-type cyclization

Authors
Shin, C; Chavre, SN; Pae, AN; Cha, JH; Koh, HY; Chang, MH; Choi, JH; Cho, YS
Issue Date
2005-07-21
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v.7, no.15, pp.3283 - 3285
Abstract
A novel synthetic methodology for 2,5-disubstituted tetrahydrofurans having an allenyl group at the 3-position via Prins-type cyclization was developed. The reaction led to excellent selectivity and moderate to high yields.
Keywords
DIASTEREOSELECTIVE SYNTHESIS; TRANS-2,5-DISUBSTITUTED TETRAHYDROFURANS; STEREOSELECTIVE-SYNTHESIS; MEDIATED CYCLIZATIONS; CONVENIENT SYNTHESIS; TETRAHYDROPYRANS; ETHERS; CARBINOLS; EPOXIDES; ALCOHOLS; DIASTEREOSELECTIVE SYNTHESIS; TRANS-2,5-DISUBSTITUTED TETRAHYDROFURANS; STEREOSELECTIVE-SYNTHESIS; MEDIATED CYCLIZATIONS; CONVENIENT SYNTHESIS; TETRAHYDROPYRANS; ETHERS; CARBINOLS; EPOXIDES; ALCOHOLS; stereoselective; tetrahydrofuran; prins type cyclization
ISSN
1523-7060
URI
https://pubs.kist.re.kr/handle/201004/136283
DOI
10.1021/ol051058r
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KIST Article > 2005
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