Organocatalytic Highly Enantioselective Monofluoroalkylation of 3-Bromooxindoles: Construction of Fluorinated 3,3′-Disubstituted Oxindoles and Their Derivatives
Organic Letters2014Vol. 16(7), pp. 1960–1963
Citations Over TimeTop 10% of 2014 papers
Abstract
A new practical organocatalytic asymmetric protocol for the introduction of a monofluoroalkyl group into the oxindole framework has been successfully developed. Excellent diastereoselectivities (>20:1 dr) and enantioselectivities (93-99% ee) of the products were obtained with a wide range of pre-electrophiles (3-bromooxindoles) and prenucleophiles (α-fluorinated β-keto gem-diols). The obtained products themselves and their derivatives may significantly benefit drug discovery.
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