Synthesis of 4-aminocyclohex-1-enecarboxylates from Danishefsky's diene

Authors
Quirante, J Vila, X Bonjoch, J
Citation
J. Quirante et al., Synthesis of 4-aminocyclohex-1-enecarboxylates from Danishefsky's diene, SYNTHESIS-S, (13), 2001, pp. 1971-1974
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
13
Year of publication
2001
Pages
1971 - 1974
Database
ISI
SICI code
0039-7881(200110):13<1971:SO4FDD>2.0.ZU;2-O
Abstract
An efficient BF3. Et2O mediated conversion of Diels-Alder adduct I of Danis hefsky's diene and methyl acrylate yielded cyclohexenones 2 and 3. Subseque nt reductive amination with several amines using NaBH(OAc)(3) in acetic aci d medium gave 4-alkylaminocyclohex-1-enecarboxylate derivatives (4a-e) in a concise form.