A new ligand scaffold for catalytic asymmetric alkylzinc additions to aldehydes.
[reaction: see text] 1,3-Azole derivatives of 2-aminocyclohexanecarboxylic acid represent a new class of bidentate ligands for metal-mediated catalytic asymmetric synthesis. N-[2-(4-Isopropyl-4,5-dihydrooxazol-2-yl)cyclohexyl]methanesulfonamide (6) is particularly well suited for the addition of alkylzinc reagents to aliphatic aldehydes in high enantiomeric excess.
Wipf
Peter
P
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf@pitt.edu
Wang
Xiaodong
X