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The asymmetric aldol reaction was carried out by deprotonating an N-propionyl derivative of alcohol-derived terpene "cis-myrtanol", chiral auxiliary with lithium diisopropylamide (LDA), and then treating the Z-lithium enolate with benzaldehyde. Unfortunately, analysis of 1 H NMR spectrum of the crude aldol product showed poor diastereoselectivity. The boron enolate methodology was adopted to improve it. The boron enolate was generated by treatment of the Npropionyl derivative with Bu2BOTf and diisopropylethylamine and then treated with benzaldehyde. Analysis of 1 H NMR spectrum of the crude aldol product obtained revealed an excellent diastereoselectivity.

Asymmetric aldol reactions of N-propionyl derivative of chiral auxiliary derived from terpene alcohol cis-myrtanol with benzaldehyde