Mukaiyama aldol addition
Also known as: Mukaiyama aldol reaction
The Mukaiyama aldol addition is an organic reaction used to convert an aldehyde and a silyl enol ether to a 1,3 ketol using a Lewis acid catalyst (such as TiCl4), followed by aqueous work-up. The mechanism begins by coordination of the aldehyde's oxygen to Titanium, which activate the carbonyl for attack while also releasing a chloride ion. The chloride attacks the silicon of the silyl enol ether to form TMSCl and an enolate. The enolate then attacks the activated carbonyl and subsequent aqueous work-up provides the final 1,3 ketol product.
Mukaiyama, T.; Narasaka, K.; Banno, K. Chem. Lett. 1973 1011–1014.
Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503–7509.