Discrimination of the Enantiotopic Faces of Structurally Unbiased Carbenium Ions Employing a Cyclohexadiene‐Based Chiral Hydride Source

• Published in: Angewandte Chemie International Edition Vol. 62; no. 29; pp. e202305295 - n/a
• Main Authors: Wolff, Benedikt, Qu, Zheng‐Wang, Grimme, Stefan, Oestreich, Martin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 17.07.2023; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alkenes; Cationic Reactions; Chemistry; Chemistry, Multidisciplinary; Density Functional Calculations; Enantiomers; Hydrides; Hydrogen bonds; Hydrogenation; Ions; Physical Sciences; Reaction mechanisms; Reduction; Science & Technology; Stereoselectivity; Styrenes; Alkenes; CARBOCATIONS; CYCLOHEXA-1,4-DIENES; ALKYLATION; B(C6F5)-CATALYZED TRANSFER; Hydrogenation; Cationic Reactions; Stereoselectivity; Density Functional Calculations; INTERMOLECULAR REACTIONS; DIHYDROGEN; 4+2 CYCLOADDITION; BASIS-SETS; S(N)1-TYPE REACTIONS

An enantioselective reduction of simple carbenium ions with cyclohexadienes containing a hydridic C−H bond at an asymmetrically substituted carbon atom is disclosed. The net reaction is a transfer hydrogenation of alkenes (styrenes) only employing chiral cyclohexadienes as dihydrogen surrogates. The...