Rhodium‐Catalyzed Domino Enantioselective Synthesis of Bicyclo[2.2.2]lactones

Abstract

Once, twice, three times a catalyst! A novel domino rhodium(I)-catalyzed asymmetric transformation of substituted oxabicyclic alkenes into bicyclo[2.2.2]lactones proceeded with good yields (up to 78 %) and excellent stereoselectivity (>97 % ee; see scheme; cod=1,5-cyclooctadiene, Tf=trifluoromethanesulfonyl). Mechanistic investigations suggest that this process proceeds by rhodium-catalyzed asymmetric ring opening, allylic alcohol isomerization and oxidation. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.