A general transition-metal-free cross-coupling
between benzylic
sulfonylhydrazones and 1°, 2°, or 3° alkyl boronic
acids is reported. The base-promoted reaction is operationally simple
and exhibits a broad substrate scope to forge a variety of alkyl–alkyl
bonds, including between sterically encumbered secondary and tertiary
sp3-carbons. The ability of this method to simplify retrosynthetic
analysis is exemplified by the improved synthesis of multiple medicinally
relevant scaffolds.
Herein we report a highly regio- and stereoselective haloazidation of allylic alcohols. This enantioselective reaction uses readily available materials and can be performed on a variety of alkyl-substituted alkenes and can incorporate either bromine or chlorine as the electrophilic halogen component. Both halide and azido groups of the resulting products can be transformed into valuable building blocks with complete stereospecificity. The first example of an enantioselective 1,4-haloazidation of a conjugated diene is reported as well as its application to a concise synthesis of an aza-sugar.
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