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 inAdvanced synthesis & catalysis Vol. 363; no. 17; pp. 4197 - 4203
Main Authors Lee, Chang Yoon, Kwon, Yong Il, Jang, Hyun Sun, Lee, Sumin, Chun, Yoo Lim, Jung, Junyang, Kim, Sung‐Gon
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.09.2021
Wiley Subscription Services, Inc
Subjects
[4+3]-Cycloaddition
Adducts
Asymmetric catalysis
Asymmetry
Azaoxyallyl cation
Benzodiazepines
Benzodiazepinone
Carbonyls
Cations
Chemistry
Chemistry, Applied
Chemistry, Organic
Cycloaddition
Degeneration
Enantiomers
Peripheral nerve degeneration
Physical Sciences
Science & Technology
[4+3]-Cycloaddition
CELLS
DESIGN
Peripheral nerve degeneration
RECEPTOR
Benzodiazepinone
Azaoxyallyl cation
INHIBITORS
ANTAGONISTS
Asymmetric catalysis
DERIVATIVES
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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.
Bibliography:These authors contributed equally to this work.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100676