Discrimination of the Enantiotopic Faces of Structurally Unbiased Carbenium Ions Employing a Cyclohexadiene‐Based Chiral Hydride Source
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...
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| Published in | Angewandte Chemie International Edition Vol. 62; no. 29; pp. e202305295 - n/a |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
17.07.2023
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Abstract | 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 trityl cation is used to initiate a Brønsted acid‐promoted process, in which a delicate intermolecular capture of a carbenium‐ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non‐covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer‐hydrogenation methods involving the cyclohexadiene platform.
A chiral cyclohexadiene‐based dihydrogen surrogate can distinguish between the enantiotopic faces of benzylic carbenium ions (see Scheme). No covalent interactions are required but instead dispersion controls the facial discrimination as verified by computations. |
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| AbstractList | 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 trityl cation is used to initiate a Brønsted acid‐promoted process, in which a delicate intermolecular capture of a carbenium‐ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non‐covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer‐hydrogenation methods involving the cyclohexadiene platform.
A chiral cyclohexadiene‐based dihydrogen surrogate can distinguish between the enantiotopic faces of benzylic carbenium ions (see Scheme). No covalent interactions are required but instead dispersion controls the facial discrimination as verified by computations. 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 trityl cation is used to initiate a Brønsted acid-promoted process, in which a delicate intermolecular capture of a carbenium-ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non-covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer-hydrogenation methods involving the cyclohexadiene platform.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 trityl cation is used to initiate a Brønsted acid-promoted process, in which a delicate intermolecular capture of a carbenium-ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non-covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer-hydrogenation methods involving the cyclohexadiene platform. 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 trityl cation is used to initiate a Bronsted acid-promoted process, in which a delicate intermolecular capture of a carbenium-ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non-covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer-hydrogenation methods involving the cyclohexadiene platform. 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 trityl cation is used to initiate a Brønsted acid‐promoted process, in which a delicate intermolecular capture of a carbenium‐ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non‐covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer‐hydrogenation methods involving the cyclohexadiene platform. 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 trityl cation is used to initiate a Brønsted acid-promoted process, in which a delicate intermolecular capture of a carbenium-ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non-covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer-hydrogenation methods involving the cyclohexadiene platform. 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 trityl cation is used to initiate a Brønsted acid‐promoted process, in which a delicate intermolecular capture of a carbenium‐ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non‐covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer‐hydrogenation methods involving the cyclohexadiene platform.Dedicated to Professor Larry E. Overman on the occasion of his 80th birthday |
| Author | Qu, Zheng‐Wang Wolff, Benedikt Oestreich, Martin Grimme, Stefan |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37158564$$D View this record in MEDLINE/PubMed |
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| Keywords | 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 |
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| Snippet | An enantioselective reduction of simple carbenium ions with cyclohexadienes containing a hydridic C−H bond at an asymmetrically substituted carbon atom is... An enantioselective reduction of simple carbenium ions with cyclohexadienes containing a hydridic C-H bond at an asymmetrically substituted carbon atom is... |
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| SubjectTerms | Alkenes Cationic Reactions Chemistry Chemistry, Multidisciplinary Density Functional Calculations Enantiomers Hydrides Hydrogen bonds Hydrogenation Ions Physical Sciences Reaction mechanisms Reduction Science & Technology Stereoselectivity Styrenes |
| Title | Discrimination of the Enantiotopic Faces of Structurally Unbiased Carbenium Ions Employing a Cyclohexadiene‐Based Chiral Hydride Source |
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