Diastereodivergent Enantioselective [8 + 2] Annulation of Tropones and Enals Catalyzed by N-Heterocyclic Carbenes

Shoulei Wang, Carles Rodríguez-Escrich, Mauro Fianchini, Feliu Maseras, Miquel A. Pericàs

Research output: Contribution to journalArticleResearch

14 Citations (Scopus)

Abstract

© 2019 American Chemical Society. N-Heterocyclic carbene catalysts are used for the first time to mediate asymmetric [8 + 2] cycloadditions of enals with tropones. The kinetic [8 + 2] cis-cycloadducts can be epimerized to their trans analogues by simply using increased amounts of base and longer reaction times. Substituted tropones are also tolerated, and the cycloaddition products can be derivatized by hydrogenation or methanolysis. The main stereochemical features of the process have been rationalized by microkinetic modeling based on the results of DFT calculations.
Original languageEnglish
Pages (from-to)3187-3192
JournalOrganic Letters
Volume21
DOIs
Publication statusPublished - 3 May 2019

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