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An oxathiaphospholane approach to one-pot phosphorothioylation of isoprenoid alcohols

, : An oxathiaphospholane approach to one-pot phosphorothioylation of isoprenoid alcohols. Organic Letters 6(9): 1385-1387

[reaction: see text] Allyl, isopentenyl, geranyl, citronellyl, farnesyl, and phytyl alcohols were transformed in good yield (>60%) into their phosphorothioates via a DBU-assisted 1,3,2-oxathiaphospholane ring-opening condensation with 2-(2-cyanoethoxy)-2-thiono-1,3,2-oxathiaphospholane, a reagent that is stable and easy to handle, followed by subsequent removal of the 2-cyanoethyl group from the intermediate phosphorothioate diester under basic conditions.


PMID: 15101748

DOI: 10.1021/ol049771o

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