An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence

[Image: see text] A strategy for synthesizing highly functionalized cyclohepta[b]indoles through a concise (4 + 3) cycloaddition–cyclization–elimination sequence is described. The cycloaddition features nitrogen-stabilized oxyallyl cations derived from epoxidations of N-aryl-N-sulfonyl-substituted a...

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Autores principales: He, Shuzhong, Hsung, Richard P., Presser, William R., Ma, Zhi-Xiong, Haugen, Bryan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998770/
https://www.ncbi.nlm.nih.gov/pubmed/24701990
http://dx.doi.org/10.1021/ol5006455
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author He, Shuzhong
Hsung, Richard P.
Presser, William R.
Ma, Zhi-Xiong
Haugen, Bryan J.
author_facet He, Shuzhong
Hsung, Richard P.
Presser, William R.
Ma, Zhi-Xiong
Haugen, Bryan J.
author_sort He, Shuzhong
collection PubMed
description [Image: see text] A strategy for synthesizing highly functionalized cyclohepta[b]indoles through a concise (4 + 3) cycloaddition–cyclization–elimination sequence is described. The cycloaddition features nitrogen-stabilized oxyallyl cations derived from epoxidations of N-aryl-N-sulfonyl-substituted allenamides, while the cyclization and elimination employed an intramolecular Grignard addition and a one-step Chugaev process, respectively.
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spelling pubmed-39987702015-04-04 An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence He, Shuzhong Hsung, Richard P. Presser, William R. Ma, Zhi-Xiong Haugen, Bryan J. Org Lett [Image: see text] A strategy for synthesizing highly functionalized cyclohepta[b]indoles through a concise (4 + 3) cycloaddition–cyclization–elimination sequence is described. The cycloaddition features nitrogen-stabilized oxyallyl cations derived from epoxidations of N-aryl-N-sulfonyl-substituted allenamides, while the cyclization and elimination employed an intramolecular Grignard addition and a one-step Chugaev process, respectively. American Chemical Society 2014-04-04 2014-04-18 /pmc/articles/PMC3998770/ /pubmed/24701990 http://dx.doi.org/10.1021/ol5006455 Text en Copyright © 2014 American Chemical Society
spellingShingle He, Shuzhong
Hsung, Richard P.
Presser, William R.
Ma, Zhi-Xiong
Haugen, Bryan J.
An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence
title An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence
title_full An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence
title_fullStr An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence
title_full_unstemmed An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence
title_short An Approach to Cyclohepta[b]indoles through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev Elimination Sequence
title_sort approach to cyclohepta[b]indoles through an allenamide (4 + 3) cycloaddition–grignard cyclization–chugaev elimination sequence
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998770/
https://www.ncbi.nlm.nih.gov/pubmed/24701990
http://dx.doi.org/10.1021/ol5006455
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