Enantioselective direct aldol reaction "on water" promoted by chiral organic catalysts.
[structure: see text]. 1,1'-Binaphthyl-2,2'-diamine-based (S)-prolinamides in the presence of stearic acid were able to promote the direct aldol condensation of cyclohexanone and other ketones with different aldehydes in the presence of a massive amount of water in very good yields, high diastereoselectivity, and up to 99% ee. The behavior of both C2- and C1-symmetric catalysts in combination with different additives was investigated, and a preliminary experiment of recovering and recycling of the catalytic system was also attempted.
Guizzetti
Stefania
S
Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy.
Benaglia
Maurizio
M
Raimondi
Laura
L
Celentano
Giuseppe
G