Synthesis of tetrahydrofurans from protected β-hydroxyaldehydes: Optimization of the alcohol protecting group

Stereoselective Synthesis of 3-Hydroxy-2-aryltetrahydrofurans from β-(Triethylsilyl)oxyaldehydes and Aryldiazomethanes

“…The stereoselectivity is consistent with that seen in the reaction of diazoesters with these same substrates …”

“…The biological importance of C -aryl glycosides has led to the development of a large number of synthetic methods for their construction. , We have recently reported a new stereoselective synthesis of 2-furanoic acids from β-(triethylsilyl)oxyaldehydes and α-diazoester, and hoped to apply this same strategy to the synthesis of deoxy C -aryl glycosides. Our progress toward this goal is presented here with the report of a new method for the synthesis of 2-aryltetrahydrofurans.…”

Stereoselective Synthesis of Tetrahydropyrans via a Formal [4 + 2]-Cycloaddition of Allylsilanes

“…Previous work from our laboratory has shown a triethylsilyl ether to be an excellent oxygen nucleophile toward reactive electrophiles under Lewis acid conditions . We hoped to develop a synthesis of tetrahydropyrans by exploiting the nucleophilicity of the triethylsilyl ether oxygen.…”

“…6 Previous work from our laboratory has shown a triethylsilyl ether to be an excellent oxygen nucleophile toward reactive electrophiles under Lewis acid conditions. 7 We hoped to develop a synthesis of tetrahydropyrans by exploiting the nucleophilicity of the triethylsilyl ether oxygen. This strategy relies on the triethylsilyl group hindering complexation of the ether oxygen with Lewis acids but still allowing it to function as a more potent nucleophile than the Lewis acid-complexed alkoxide ion.…”

Saturated oxygen heterocycles

“…Thus, reaction of benzyl diazoacetate with silyl-protected β-hydroxyaldehydes gave 119, the gem-dimethyl group proving advantageous for high yield (Scheme 69). With no methyl groups the yields were extremely low, 170 but only a single alkyl group in this position provided moderate to good yields of the tetrahydrofurans with good stereocontrol. 171 Molander and Haas have used a combination of [3 ϩ 4] annulation and ozonolysis to prepare racemic davanone.…”