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

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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… Click to show full 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.

Keywords: closing metathesis; aza henry; ring closing; synthesis

Journal Title: Organic letters
Year Published: 2023

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