Brønsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo‐ and Enantioselective Synthesis of Spirolactams
Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom‐economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectiviti...
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| Published in | Angewandte Chemie International Edition Vol. 60; no. 52; pp. 27164 - 27170 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
20.12.2021
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Abstract | Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom‐economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]‐rearrangement is shown to be kinetically preferred over the related [1,3]‐rearrangement by theoretical calculations.
A Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement is disclosed that involves an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds and allows the practical and atom‐economic synthesis of various valuable spirolactams. Moreover, the asymmetric version of this tandem cyclization is also achieved via kinetic resolution by chiral phosphoric acid catalysis. |
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| AbstractList | Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]-rearrangement is shown to be kinetically preferred over the related [1,3]-rearrangement by theoretical calculations. Described herein is a novel Bronsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]-rearrangement is shown to be kinetically preferred over the related [1,3]-rearrangement by theoretical calculations. Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]-rearrangement is shown to be kinetically preferred over the related [1,3]-rearrangement by theoretical calculations.Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]-rearrangement is shown to be kinetically preferred over the related [1,3]-rearrangement by theoretical calculations. Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom‐economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]‐rearrangement is shown to be kinetically preferred over the related [1,3]‐rearrangement by theoretical calculations. A Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement is disclosed that involves an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds and allows the practical and atom‐economic synthesis of various valuable spirolactams. Moreover, the asymmetric version of this tandem cyclization is also achieved via kinetic resolution by chiral phosphoric acid catalysis. |
| Author | Zhou, Bo Chen, Peng‐Fei Wang, Binju Wu, Peng Ye, Long‐Wu |
| Author_xml | – sequence: 1 givenname: Peng‐Fei surname: Chen fullname: Chen, Peng‐Fei organization: Xiamen University – sequence: 2 givenname: Bo surname: Zhou fullname: Zhou, Bo organization: Xiamen University – sequence: 3 givenname: Peng surname: Wu fullname: Wu, Peng organization: Xiamen University – sequence: 4 givenname: Binju surname: Wang fullname: Wang, Binju organization: Xiamen University – sequence: 5 givenname: Long‐Wu orcidid: 0000-0003-3108-2611 surname: Ye fullname: Ye, Long‐Wu email: longwuye@xmu.edu.cn organization: Nankai University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/34672067$$D View this record in MEDLINE/PubMed |
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| Keywords | ASYMMETRIC-SYNTHESIS HYDROGENATION alkynes OXINDOLES CLAISEN REARRANGEMENT INDOLES cyclizations YNAMIDES REDUCTION heterocycles kinetic resolution INHIBITORS Bronsted acids ACCESS Brønsted acids |
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| Snippet | Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom‐economic synthesis... Described herein is a novel Bronsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis... Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis... |
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| SubjectTerms | alkynes Aromatic compounds Atom economy Brønsted acids Catalysis Chemistry Chemistry, Multidisciplinary cyclizations Enantiomers heterocycles Heterocyclic compounds kinetic resolution Nucleotide sequence Phosphoric acid Physical Sciences Science & Technology Substrates |
| Title | Brønsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo‐ and Enantioselective Synthesis of Spirolactams |
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