Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 24, Pages 8084-8088Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601548
Keywords
azomethines; carbamates; cycloaddition; organocatalysis; tetrahydroisoquinolines
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
- European Union [PIIF-GA-2013-622134]
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The first catalytic asymmetric inverse electron demand 1,3-dipolar cycloaddition of azomethine imines with enecarbamates has been developed. Isoquinoline-fused pyrazolidines containing two or three contiguous stereogenic centers were obtained in high yields with excellent regio-, diastereo-, and enantioselectivities. The pyrazolidine ring can be opened to install an aminal, alpha-amino nitrile, or homoallylamine function with an excellent control of the newly generated stereogenic center. Access to aminobenzo[a]quinolizidine is also documented.
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