Dispiroketals in synthesis. Part 24.¹ Preparation and use of chiral 2,2′-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s as new protecting and resolving agents for 1,2-diols

Abstract

C₂ symmetric chiral 2,2′-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s (S,S )-1 and (R,R)-1 were prepared from the corresponding glycidols and selectively reacted with 1,2-diols to give dispiroketals. The products of these reactions could be deprotected following treatment with fluoride, oxidation and reductive cleavage with samarium(II) iodide.

References

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