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Enantioselective Synthesis of cis- and trans-Cycloheptyl β-Fluoro Amines by Sequential aza-Henry Addition/Ring-Closing Metathesis.

ABSTRACT: The synthesis of 7-membered carbocyclic β-fluoroamines is accomplished by a combination of the enantioselective aza-Henry reaction of aliphatic N-Boc imines and ring-closing metathesis. Use of reductive denitration gives both diastereomers of the β-fluoro amine carbocycle, each with high enantiomeric excess.

SUBMITTER: Bing JA 

PROVIDER: S-EPMC10240541 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of <i>cis</i>- and <i>trans</i>-Cycloheptyl β-Fluoro Amines by Sequential aza-Henry Addition/Ring-Closing Metathesis.

Bing Jade A JA   Johnston Jeffrey N JN  

Organic letters 20230203 6

The synthesis of 7-membered carbocyclic β-fluoroamines is accomplished by a combination of the enantioselective aza-Henry reaction of aliphatic <i>N</i>-Boc imines and ring-closing metathesis. Use of reductive denitration gives both diastereomers of the β-fluoro amine carbocycle, each with high enantiomeric excess. ...[more]

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