Tetrahedron p. 5593 - 5608 (1997)
Update date:2022-07-29
Topics:
Gennari, Cesare
Moresca, Daniela
Vulpetti, Anna
Pain, Gilles
Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences. With thioacetate-derived chiral enolates and enantiopure N,N-dibenzyl α-amino aldehydes, either the 3,4- anti or the 3,4-syn aldol adduct can be obtained with very high diastereoselectivity just by changing the chiral boron ligand configuration. The above procedure was used for a stereoselective total synthesis of (3S,4S)-statine.
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