Raymond Baker, José L. Castro, Christopher John Swain
1988
Citations
0
Influential Citations
10
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Reactions of 3-nitro-2-methoxybenzaldehydes with the boron enolate of a chiral propionyl oxazolidone has been demonstrated to yield poor diastereoselection in the presence of i -Pr 2 NEt as base whereas the use of Et 3 N results in 98% diastereoselection. The nature of the ammonium salt formed on production of the enolate appears to play some role in the transition state for reaction with the aldehyde.