[reaction: see text] Treatment of a variety of alcohols, amines, and N-hydroxylamines with 2,2,2-trifluoroethyl formate gave the corresponding formylated adducts in high yields.
The stereoselective arylation of hydroxy protected 1,6-anhydro-β-d-glucose with arylalanes to provide β-C-arylglucosides is reported. Modification of triarylalanes, Ar3Al, with strong Brønsted acids (HX) or AlCl3 produced more reactive arylating agents, Ar2AlX, while the incorporation of alkyl dummy ligands into the arylating agents was also viable. Me3Al and i-Bu2AlH were found useful in the in situ blocking of the C3-hydroxyl group of 2,4-di-O-TBDPS protected 1,6-anhydroglucose. The utility of the method was demonstrated by the synthesis of the SGLT2 inhibitor, canagliflozin.
225ChemInform Abstract The title compound (I) is converted by n-butyllithium (II) into its 1-lithio derivative (III) which is alkylated to yield the substituted alkanes (V). Repetition of this procedure gives the dialkylated products (VII). Elimination reaction of (V) and (VII) with tetrabutylammonium fluoride produces the corresponding terminal olefins (VIII). The allyltrimethylsilanes (X) are prepared from (III) and the carbonyl compounds (IX) by a method described earlier. Reductive debenzenesulfonylation of (XII), obtained from (III) and the aldehydes (XI), results in the formation of the β-trimethylsilyl ketones (XIII). Reaction of (III) with the epoxides (XIV) gives intermediate adducts which are converted via mesylates to the cyclopropanes (XV). Further reactions with (III) or (V) are described in the original paper.
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