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Solution-phase automated synthesis of an ?-amino aldehyde as a versatile intermediate.

ABSTRACT: A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.

SUBMITTER: Masui H

PROVIDER: S-EPMC5301908 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate.

Masui Hisashi H Yosugi Sae S Fuse Shinichiro S Takahashi Takashi T

Beilstein journal of organic chemistry 20170117

A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. <i>tert</i>-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection. ...[more]

PMID: 28228851

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