Acetic acid-promoted cascade N-acyliminium ion/aza-Prins cyclization: stereoselective synthesis of functionalized fused tricyclic piperidines

A novel acetic acid-promoted metal-free cascade N-acyliminium ion/aza-Prins cyclization of o-formyl carbamates and homoallylamines is reported. This one-pot protocol provides efficient and rapid access to masked cis-hydroxyhexahydropyrido[1,2-c]quinazolin-6-ones with concomitant generation of two st...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017, Vol.53 (13), p.2110-2113
Main Authors: Sawant, Rajiv T, Stevens, Marc Y, Odell, Luke R
Format: Article
Language:English
Subjects:
Carbon-carbon composites
Cascades
Chemical bonds
Piperidine
Synthesis (chemistry)
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Summary:A novel acetic acid-promoted metal-free cascade N-acyliminium ion/aza-Prins cyclization of o-formyl carbamates and homoallylamines is reported. This one-pot protocol provides efficient and rapid access to masked cis-hydroxyhexahydropyrido[1,2-c]quinazolin-6-ones with concomitant generation of two stereogenic centers, four C-C/C-O/C-N bonds and two new rings in good yield and excellent diastereoselectivity.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c6cc09805c