Cyclization of N -Boc-( E )-α,β-unsaturated γ-amino acid active esters into N -Boc-( Z )-α,β-unsaturated γ-lactams through E → Z isomerization

Here, we are reporting the spontaneous transformation of the active esters of -Boc protected -α,β-unsaturated γ-amino acids into the corresponding -α,β-unsaturated γ-lactams with concomitant → isomerization in the presence of a weak base. No cyclization was observed in the absence of the base. Analy...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-05, Vol.21 (18), p.3766-3769
Main Authors: Singh, Manjeet, Kumar, Manish, Nalawade, Sachin A, Puneeth Kumar, DRGKoppalu R, Gopi, Hosahudya N
Format: Article
Language:English
Subjects:
Amino acids
Esters
Isomerization
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Summary:Here, we are reporting the spontaneous transformation of the active esters of -Boc protected -α,β-unsaturated γ-amino acids into the corresponding -α,β-unsaturated γ-lactams with concomitant → isomerization in the presence of a weak base. No cyclization was observed in the absence of the base. Analysis revealed that amide γ-NH is crucial for both lactamization and → isomerization. This mild transformation provides easy access to the synthetically challenging α,β-unsaturated γ-lactams and also gives new insights into the → isomerization of double bonds.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00127j