A Photochemical Route to 3- and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry.

doi:10.1021/acs.joc.7b02559

Paper

A Photochemical Route to 3- and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry.

Published Jan 5, 2018 · Zong Chang, France Boyaud, R. Guillot

The Journal of organic chemistry

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13

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Abstract

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.

Study Snapshot

This study presents a photochemical route for the synthesis of 3- and 4-hydroxy derivatives of 2-aminocyclobutane-1-carboxylic acid with an all-cis geometry, using highly endo-selective photocycloaddition reactions and regioselective ring

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

A Photochemical Route to 3- and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry.

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