Organocatalytic Enantioselective [4+3]‐Cycloadditions of Azaoxyallyl Cations with 2‐Aminophenyl Enones

The first organocatalytic asymmetric [4+3]‐cycloaddition of 2‐aminophenyl α,β‐unsaturated carbonyls with in situ generated azaoxyallyl cations was developed, and enantioenriched functionalized seven‐membered 1,4‐benzodiazepine‐3‐ones were obtained in good yields and with excellent enantioselectiviti...

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Published in:Advanced synthesis & catalysis 2021-09, Vol.363 (17), p.4197-4203
Main Authors: Lee, Chang Yoon, Kwon, Yong Il, Jang, Hyun Sun, Lee, Sumin, Chun, Yoo Lim, Jung, Junyang, Kim, Sung‐Gon
Format: Article
Language:English
Subjects:
[4+3]-Cycloaddition
Adducts
Asymmetric catalysis
Asymmetry
Azaoxyallyl cation
Benzodiazepines
Benzodiazepinone
Carbonyls
Cations
Cycloaddition
Degeneration
Enantiomers
Peripheral nerve degeneration
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cited_by cdi_FETCH-LOGICAL-c3176-681c0d57630d74397ce7db0b74511887e26fcfcf0850b2732c83dd3da2d8a27e3
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container_issue 17
container_start_page 4197
container_title Advanced synthesis & catalysis
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creator Lee, Chang Yoon
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description The first organocatalytic asymmetric [4+3]‐cycloaddition of 2‐aminophenyl α,β‐unsaturated carbonyls with in situ generated azaoxyallyl cations was developed, and enantioenriched functionalized seven‐membered 1,4‐benzodiazepine‐3‐ones were obtained in good yields and with excellent enantioselectivities. This approach was also extended to the first asymmetric [4+3]‐cycloaddition of δ‐hydroxy α,β‐unsaturated carbonyls, affording 1,4‐oxazepanes in one step under mild conditions. Several of the novel adducts demonstrated promising bioactivity in the prevention of peripheral nerve degeneration.
doi_str_mv 10.1002/adsc.202100676
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subjects [4+3]-Cycloaddition
Adducts
Asymmetric catalysis
Asymmetry
Azaoxyallyl cation
Benzodiazepines
Benzodiazepinone
Carbonyls
Cations
Cycloaddition
Degeneration
Enantiomers
Peripheral nerve degeneration
title Organocatalytic Enantioselective [4+3]‐Cycloadditions of Azaoxyallyl Cations with 2‐Aminophenyl Enones
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