%ANi, Dongshun [Department of Chemistry Indiana University 800 E. Kirkwood Ave. Bloomington IN 47401 USA]%AWitherspoon, Brittany [Current Address: Janssen Research &, Development, LLC 3210 Merryfield Row San Diego CA 92121 USA]%AZhang, Hong [Department of Chemistry and Biochemistry University of California Los Angeles CA 90095 USA, Current Address: College of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 China]%AZhou, Chen [Department of Chemistry Indiana University 800 E. Kirkwood Ave. Bloomington IN 47401 USA]%AHouk, K. [Department of Chemistry and Biochemistry University of California Los Angeles CA 90095 USA]%ABrown, M. [Department of Chemistry Indiana University 800 E. Kirkwood Ave. Bloomington IN 47401 USA]%BJournal Name: Angewandte Chemie; Journal Volume: 132; Journal Issue: 28; Related Information: CHORUS Timestamp: 2023-09-03 09:50:00 %D2020%IWiley Blackwell (John Wiley & Sons) %JJournal Name: Angewandte Chemie; Journal Volume: 132; Journal Issue: 28; Related Information: CHORUS Timestamp: 2023-09-03 09:50:00 %K %MOSTI ID: 10149514 %PMedium: X %TStereoselective [4+2]‐Cycloaddition with Chiral Alkenylboranes %XAbstract

A method for the stereoselective [4+2]‐cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N‐protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C−B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.

%0Journal Article