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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Bibliographic Details
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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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100676