Published TCIMAIL newest issue No.197
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Boron-Mediated Aldol Reaction
No.120(June 2004)
Boron-mediated Aldol reaction proceeds by reacting boron triflate with carbonyl compounds to form a complex. The complex is deprotonated at α-position by amine to form an enolate. Boron triflate derivative 1 possesses bulky cyclohexyl groups. Therefore, when triethylamine is added, anti-selective aldol adducts are obtained, whereas syn-selective aldol adducts gets produced upon addition of ethyldiisopropylamine. Abiko and corworkers have found that the reaction between propionate esters bonded with chiral auxiliaries and isobutyraldehyde in the presence of 1 and triethylamine forms high anti-selectivitie Aldol adducts with diastereoselectivities.1)
References
- 1)anti- and syn-Selective asymmetric aldol reactions
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