Diastereoselective Coupling of Chiral Acetonide Trisubstituted Radicals with Alkenes. Issue 26 (30th May 2016)

• Record Type: Journal Article
• Authors: Tao, Daniel J.; Muuronen, Mikko; Slutskyy, Yuriy; Le, Alexander; Furche, Filipp; Overman, Larry E.
• Is Part Of: Chemistry. Volume 22:Issue 26(2016)
• Page Start: 8786
• Page End: 8790
• Publication Date: 2016-05-30
• Subjects: ab initio calculations -- alkenes -- radical reactions -- stereoselectivity; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201601957
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The stereochemical outcome of reactions of chiral nucleophilic trisubstituted acetonide radicals with electron‐deficient alkenes is dictated by a delicate balance between destabilizing non‐bonding interactions and stabilizing hydrogen‐bonding between substituents on the α and β carbons. Abstract : Connecting the dots : The origins of diastereoselective radical conjugate additions with monocyclic trisubstituted acetonide carbon radicals (see scheme) were investigated both experimentally and computationally.