Stereoselectivity in the intramolecular Nozaki–Hiyama–Kishi reaction: influence of the substitution pattern and protecting groups in the construction of 10-membered lactones

Abstract

The use of the intramolecular Nozaki–Hiyama–Kishi reaction to construct 10-membered lactones is described. The influence of the nature of the protecting groups at C3 and C4 and the presence of the methyl group at C9 on the stereochemistry of the newly formed stereogenic center at C7 was investigated. Matched induction led to the preparation of the decanolide moiety with high degree of stereoselection.