An Efficient Petasis Boronic–Mannich Reaction of Chiral Lactol Derivatives Prepared from d-Araboascorbic Acid

Abstract

Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis­ boronic–Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from d-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.

Key words

asymmetric synthesis - chiral pool - coupling - diastereoselectivity - domino reaction - lactones

• References

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