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  • Synthesis of azabicyclo[n.1.0]alkane-derived bifunctional building blocks via the Corey–Chaykovsky cyclopropanation

Synthesis of azabicyclo[n.1.0]alkane-derived bifunctional building blocks via the Corey–Chaykovsky cyclopropanation

Tetrahedron Lett. 2018, 59 (52), 4611-4615

DOI: 10.1016/j.tetlet.2018.11.047

Yarmoliuk D.; Serhiichuk D.; Smyrnov V.; Tymtsunik A.; Hryshchuk O.; Kuchkovska Y.; Grygorenko O.

An efficient approach towards the synthesis of monoprotected azabicyclo[5.1.0]octane-derived conformationally restricted γ-amino acids and diamines is reported. Optimization of the conditions for the key Corey–Chaykovsky reaction allowed the construction of two isomeric methanoazepane frameworks on a multigram scale in 55–65% yield. Additionally, the developed approach was used in the three-step synthesis of 3,4-methano-β-proline and its diamine derivatives.

Synthesis of azabicyclo[n.1.0]alkane-derived bifunctional building blocks via the Corey–Chaykovsky cyclopropanation

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