Ontology highlight
ABSTRACT:
SUBMITTER: Tsai AS
PROVIDER: S-EPMC3640598 | biostudies-literature | 2013 Apr
REPOSITORIES: biostudies-literature
Tsai Andy S AS Chen Ming M Roush William R WR
Organic letters 20130313 7
A chiral phosphoric acid catalyzed kinetic resolution/allenylboration of racemic allenylboronates with aldehydes is described. Allenylboration of aldehydes with 2.8 equiv of allenylboronate (±)-1 in the presence of 10 mol % of catalyst (R)-2 provided anti-homopropargyl alcohols 3 in 83-95% yield with 9:1 to 20:1 diastereoselectivity and 73-95% ee. The catalyst enables the kinetic resolution of the racemic allenylboronate (±)-1 to set the methyl stereocenter and biases the facial attack of the al ...[more]