Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates.

ABSTRACT: Unlike many reactions of their six-membered-ring counterparts, the reactions of chiral seven-membered-ring enolates are highly diastereoselective. Diastereoselectivity was observed for a range of substrates, including lactam, lactone, and cyclic ketone derivatives. The stereoselectivity arises from torsional and steric interactions that develop when electrophiles approach the diastereotopic π-faces of the enolates, which are distinguished by subtle differences in the orientation of nearby atoms of the ring.

SUBMITTER: Lavinda O 

PROVIDER: S-EPMC8940697 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature