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- W2952957029 abstract "The synthesis of spiroacetals [3R*,5S*,6S*]-3-benzyloxy-5-methoxy-1,7-dioaxaspiro[5.5]undecane 3 and [3R*,5S*,6S*]-3-methoxy-5-benzyloxy-1,7-dioaxaspiro[5.5]undecane 4, where the substituents on the spiroacetal assembly are in a 1,3-diaxial orientation, is described. Epoxidation of unsaturated spiroacetal 5 using dimethyldioxirane showed greater preference for the α-epoxide 11 over the β-epoxide 12. Treatment of the α-epoxide 11 with lithium diethylamide in tetrahydrofuran afforded both the allylic alcohol 7 and the homoallylic alcohol 13 in approximately equal amounts. Use of a nonpolar solvent (hexane) suppressed the isomerization of the allylic alcohol 7 to the homoallylic alcohol 13, affording a 21:1 ratio of 7:13. Coordination of an oxygen lone pair with the electron-deficient lithium center of the reagent sets up a transition state in which abstraction of a syn-proton and opening of the epoxide leads to stereoselective formation of allylic alcohol 7 with a pseudoaxial hydroxyl group at C-5. The hydr..." @default.
- W2952957029 created "2019-06-27" @default.
- W2952957029 creator A5000579140 @default.
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- W2952957029 date "2010-06-21" @default.
- W2952957029 modified "2023-09-26" @default.
- W2952957029 title "ChemInform Abstract: Synthesis and Herbicidal Activity of [3R*,5S*,6S*]-3-Benzyloxy-5-methoxy-1,7-dioxaspiro[5.5]undecane and [3R*,5S*,6S*]-3-Methoxy-5-benzyloxy-1,7-dioxaspiro[5.5]undecane." @default.
- W2952957029 cites W2054587145 @default.
- W2952957029 doi "https://doi.org/10.1002/chin.199826168" @default.
- W2952957029 hasPublicationYear "2010" @default.
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