Literature DB >> 35076978

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

Olga Lavinda1, Collin H Witt1, K A Woerpel1.   

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.
© 2022 Wiley-VCH GmbH.

Entities:  

Keywords:  Conformational Analysis; Diastereoselectivity; Enolates; Seven-Membered-Rings; Torsional Strain

Mesh：

Substances：

Year:  2022        PMID： 35076978      PMCID： PMC8940697          DOI： 10.1002/anie.202114183

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  29 in total

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