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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.