We report a novel and practical method for the synthesis of homoallylic alcohols as well as the first asymmetric allylation of ketones using a trifluoroborate reagent. Inspired by ad-mix used in the Sharpless asymmetric dihydroxylation, we present BTF-mix, a mixture of bench-stable allyl trifluoroborate salt and a chiral biphenol (BINOL) catalyst to easily facilitate the synthesis of homoallylic alcohols in high yields and enantioselectivies (up to 99:1 e.r.), with an expanded substrate scope including cyclic ketones. Additional trifluoroborate salts, including vinyl- and methallyl- salts, are utilized in respective BINOL-trifluoroborate mixes to enable addition to ketone groups in order to synthesize asymmetric products and drug candidate precursors.

Asymmetric addition of trifluoroborate salts to ketones catalyzed by chiral biphenols

ACS Spring Meeting 2021

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