Tandem cycloaddition chemistry of nitroalkenes: Preparative and theoretical studies on the stereochemical course of [3 + 2] cycloaddition of cyclic nitronates

Scott E Denmark, Mark Seierstad, B. Herbert

Research output: Contribution to journalArticle

Abstract

Intermolecular [3 + 2] cycloadditions between two cyclic nitronates and a series of dipolarophiles are examined. High facial selectivity is observed in all cases and is analyzed with the aid of ab initio transition structure calculations. Monosubstituted dipolarophiles reacted with exclusive regiocontrol. Disubstituted dipolarophiles reacted with varying degrees of regiocontrol, which was dependent on the substituent. A theoretical approach for predicting regioselectivity is discussed. Exo selectivity was generally favored due to steric effects, and was especially high with cis-disubstituted dipolarophiles.

Original languageEnglish (US)
Pages (from-to)884-901
Number of pages18
JournalJournal of Organic Chemistry
Volume64
Issue number3
DOIs
StatePublished - Feb 5 1999

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Tandem cycloaddition chemistry of nitroalkenes: Preparative and theoretical studies on the stereochemical course of [3 + 2] cycloaddition of cyclic nitronates'. Together they form a unique fingerprint.

  • Cite this