1427165-75-0Relevant academic research and scientific papers
Chiral Bronsted acid catalyzed enantioselective synthesis of anti -homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates
Tsai, Andy S.,Chen, Ming,Roush, William R.
, p. 1568 - 1571 (2013/07/05)
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 aldehyde to set the stereochemistry of the hydroxyl group in 3.
