Tetrahedron p. 2411 - 2424 (1990)
Update date:2022-08-10
Topics:
Margot, Christian
Rizzolio, Michele
Schlosser, Manfred
Lithium diisopropylamide in the presence of catalytic amounts of potassium tert-butoxide smoothly converts homoallyl or homobenzyl type ethers to dienes (e.g., 1, 3, 5, 26) or styrenes (2). γ,δ-Unsaturated acetals give 1,3-dienyl ethers (e.g., 4) and 4-alkylidenetetrahydropyrans or dihydropyrans produce a variety of dienols (e.g., 6 - 17, 20 - 22). - If there is a choice, the new double bond is formed with high trans-selectivity while the configuration of existing double bonds is retained. - The elimination mode is syn-periplanar and concerted, though E1cb like.
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