Allyboronic acids are synthetically very useful and can easily be synthesized from allylic alcohols.1 We have disclosed unprecedented reactivity of allylboronic acids with broad variety of carbonyl compounds. These compounds react with ketones and a-keto acids under very mild conditions and allow to construct highly diastereoselective homoallylic alcohols with adjacent tertiary and quaternary centers.2Fig 1: Synthesis of stereoselcetive homoallylic alcohols We believe that general anti selectivity is the result of tight six-membered transition state (TS1) where large group around the carbonyl carbon take equatorial position. In contrary, a-keto acids react via bicyclic transition state (TS2) where R group forced to take equatorial position irrespective to spatial extent. Fig 2: Proposed transition states which give different selectivity References: 1. Raducan, M.; Alam, R.; Szab�, K. J. Angew. Chem. Int. Ed. 2012 , 51, 13050.2. Alam, R.; Raducan, M.; Eriksson, L; Szab�, K. J. (Submitted)

Diastereoselective allylboration of wide variety of carbonyl compounds using allylboronic acids: Construction of adjacent tertiary and quaternary centers

246th National Meeting (2013)

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