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Preparation and in situ use of unstable N-alkyl ?-diazo-?-butyrolactams in RhII-catalyzed X-H insertion reactions.

ABSTRACT: N-Alkyl ?-diazo-?-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X-H insertion products with alcohols, aromatic amines and thiols via an in situ RhII-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reactions tended to yield enamine adducts.

SUBMITTER: Eremeyeva M

PROVIDER: S-EPMC7136545 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X-H insertion reactions.

Eremeyeva Maria M Zhukovsky Daniil D Dar'in Dmitry D Krasavin Mikhail M

Beilstein journal of organic chemistry 20200402

N-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X-H insertion products with alcohols, aromatic amines and thiols via an in situ RhII-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reactions tended to yield enamine adducts. ...[more]

PMID: 32280388

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