Synthesis of Spirocyclopropyl γ‐Lactams by a Highly Stereoselective Tandem Intramolecular Azetidine Ring‐Opening/Closing Cascade Reaction | Zendy

Nocquet PierreAntoine | Zendy; Hazelard Damien | Zendy; Compain Philippe | Zendy

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Synthesis of Spirocyclopropyl γ‐Lactams by a Highly Stereoselective Tandem Intramolecular Azetidine Ring‐Opening/Closing Cascade Reaction

Author(s) -

Nocquet PierreAntoine,

Hazelard Damien,

Compain Philippe

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201101278

Subject(s) - azetidine , chemistry , stereoselectivity , intramolecular force , cascade reaction , ketene , stereochemistry , alkylation , nucleophile , ring (chemistry) , intramolecular reaction , medicinal chemistry , organic chemistry , catalysis

A new tandem intramolecular azetidine ring‐opening/closing cascade reaction affording spirocyclopropyl γ‐lactams in high regio‐ and stereoselectivity is reported. The key step of the process is an S N 2‐type ring‐opening of TMSOTf‐activated azetidine rings by silyl ketene acetals generated by treatment with TMSOTf and triethylamine. This study is a very rare example of nucleophilic ring opening of azetidines that does not require formation of quaternary azetidinium salts by N ‐alkylation or the use of N ‐electron‐withdrawing groups.

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