Epoxy alcohol rearrangements: hydroxyl-mediated delivery of Lewis acid promoters
DJ Morgans Jr, KB Sharpless…
Index: Morgans,D.J.; Sharpless,K.B. Journal of the American Chemical Society, 1981 , vol. 103, p. 462
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Citation Number: 72
Abstract
This substrate (erythro-threo mixture) was transformed to cis-diol z2s3 and up to 15% of another cyclic diol, presumably 3, upon treatment with OV (OEt) 3 (CH2C12, room temperature, 10 h). We were unable to detect frans-diols or either starting epoxy alcohol diastereomer. Furthermore, examination4 of the reaction mixture before disappearance of the epoxy alcohols revealed that the epoxylinalool remaining was substantially enriched ...
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