Ytterbium Triflate Catalyzed Synthesis of Alkoxy-Substituted Donor−Acceptor Cyclobutanes and Their Formal [4 + 2] Cycloaddition with Imines: Stereoselective Synthesis of Piperidines | Zendy

Mahmoud M. Abd Rabo Moustafa | Zendy; Brian L. Pagenkopf | Zendy

Open Access

Ytterbium Triflate Catalyzed Synthesis of Alkoxy-Substituted Donor−Acceptor Cyclobutanes and Their Formal [4 + 2] Cycloaddition with Imines: Stereoselective Synthesis of Piperidines

Author(s) -

Mahmoud M. Abd Rabo Moustafa,

Brian L. Pagenkopf

Publication year - 2010

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol102062t

Subject(s) - cyclobutanes , chemistry , cyclobutane , stereoselectivity , cycloaddition , annulation , trifluoromethanesulfonate , alkoxy group , catalysis , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry) , alkyl

A new synthesis of 2-alkoxy-1,1-cyclobutane diesters and their first use in dipolar cycloadditions is reported. Both the formation of the donor-acceptor cyclobutanes and their subsequent annulation with in situ formed imines are catalyzed by Yb(OTf)(3). Cyclobutanes with carbon donor groups give piperidines with high trans stereoselectivity.

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