Direct Hydroxymethylation Using Formaldehyde

Significance

A practical amine 1 catalyzed asymmetric hydroxymethylation of aldehydes with formaldehyde is reported. Further reaction of the desired hydroxyaldehyde resulted in its hemiacetal equivalent 2 as the product, incorporating a second equivalent of formaldehyde. Due to the instability, this species was transformed into the corresponding carboxylic acids 3 or the protected alcohols 4, respectively.