A photochemical route to 3- and 4-hydroxy derivatives of 2-aminocyclobutane-1-carboxylic acid with an all-cis geometry

A photochemical route to 3- and 4-hydroxy derivatives of 2-aminocyclobutane-1-carboxylic acid with an all-cis geometry

Short gram scale syntheses of both enantiomers of 2-amino-3-hydroxycyclobutane-1-carboxylic acid and of 2-amino-4-hydroxycyclobutanecarboxylic acid with an all-cis geometry are described. The sequences feature highly endo-selective [2+2]-photocycloaddition reactions followed by fully regioselective...

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Veröffentlicht in:Journal of organic chemistry 2018-01, Vol.83 (1), p.527-534
Hauptverfasser: Chang, Zong, Boyaud, France, Guillot, Régis, Boddaert, Thomas, Aitken, David J
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container_issue 1
container_start_page 527
container_title Journal of organic chemistry
container_volume 83
creator Chang, Zong
Boyaud, France
Guillot, Régis
Boddaert, Thomas
Aitken, David J
description Short gram scale syntheses of both enantiomers of 2-amino-3-hydroxycyclobutane-1-carboxylic acid and of 2-amino-4-hydroxycyclobutanecarboxylic acid with an all-cis geometry are described. The sequences feature highly endo-selective [2+2]-photocycloaddition reactions followed by fully regioselective ring opening / Hofmann rearrangement / nitrogen protection, in a consecutive or one-pot protocol, followed by efficient resolution using a chiral oxazolidinone.
doi_str_mv 10.1021/acs.joc.7b02559
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title A photochemical route to 3- and 4-hydroxy derivatives of 2-aminocyclobutane-1-carboxylic acid with an all-cis geometry
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