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 2NEt as base whereas the use of Et 3N 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.
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