☆ 4.7 Article

Synthesis of All Four Stereoisomers of 3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic Acid

JOURNAL OF ORGANIC CHEMISTRY (2013)

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JOURNAL OF ORGANIC CHEMISTRY

卷 78, 期 18, 页码 9328-9339

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AMER CHEMICAL SOC

DOI: 10.1021/jo4013282

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Chemistry, Organic

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A synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid has been developed, thereby significantly shortening the known literature procedures for the syntheses of these unnatural amino acids. With a simple adjustment of the reaction conditions, we were able to obtain either pure cis or trans acid. Optical resolution was accomplished via diastereomeric salt formation or alternatively via chromatography on a chiral stationary phase. Finally, ab initio calculations gave an explanation for the observed cis selectivity in the initial step.

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