Organocatalytic Enantioselective [4+3]‐Cycloadditions of Azaoxyallyl Cations with 2‐Aminophenyl Enones. Issue 17 (1st August 2021)

• Record Type: Journal Article
• Authors: Lee, Chang Yoon; Kwon, Yong Il; Jang, Hyun Sun; Lee, Sumin; Chun, Yoo Lim; Jung, Junyang; Kim, Sung‐Gon
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 17(2021)
• Page Start: 4197
• Page End: 4203
• Publication Date: 2021-08-01
• Subjects: Asymmetric catalysis -- [4+3]-Cycloaddition -- Azaoxyallyl cation -- Benzodiazepinone -- Peripheral nerve degeneration; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100676
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :