Enantioselective 1,3‐Dipolar Cycloaddition of Nitrones with Ethyl Vinyl Ether: The Difference between Brønsted and Lewis Acid Catalysis | Zendy

Jiao Peng | Zendy; Nakashima Daisuke | Zendy; Yamamoto Hisashi | Zendy

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Enantioselective 1,3‐Dipolar Cycloaddition of Nitrones with Ethyl Vinyl Ether: The Difference between Brønsted and Lewis Acid Catalysis

Author(s) -

Jiao Peng,

Nakashima Daisuke,

Yamamoto Hisashi

Publication year - 2008

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200705314

Subject(s) - enantioselective synthesis , cycloaddition , lewis acids and bases , catalysis , 1,3 dipolar cycloaddition , chemistry , brønsted–lowry acid–base theory , ether , organic chemistry , vinyl ether , polymer chemistry , copolymer , polymer

Brønsted and Lewis face off : A new chiral N ‐triflyl phosphoramide is used for asymmetric 1,3‐dipolar cycloaddition of diaryl nitrones to ethyl vinyl ether to give the endo products in up to 93 % ee (see scheme; Tf=trifluoromethanesulfonyl; Ad=adamantyl). The structure of the chiral phosphoramide was confirmed by X‐ray crystallographic analysis.

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