OsO 4 -Catalyzed oxidative cyclization of geranyl and NERYL ACETATE (cas 141-12-8) to cis-2,5-bis(hydroxymethyl)tetrahydrofurans

Add time:10/01/2019    Source:infona.pl

OsO 4 catalyzes the oxidative cyclization of the 1,5-dienes geranyl acetate (1) and NERYL ACETATE (cas 141-12-8) (2) to the cis-2,5-bis(hydroxymethyl)tetrahydrofurans 3 and 4 respectively, in the presence of NaIO 4 as cooxidant in DMF. The reaction is stereospecific and proceeds with the sequential syn addition to both double bonds of the starting materials. The observed stereoselectivity can be explained by invoking the intermediacy of a square-based pyramidal osmium (VI) diester (5) that has been isolated and characterized. Evidence is reported that this substance is indeed an intermediate in the transformation of 1 to 3.

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