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Highly Substituted Furo[3,4‐ d ][1,2]oxazines: Gold‐Catalyzed Regiospecific and Diastereoselective 1,3‐Dipolar Cycloaddition of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones with Nitrones
Author(s) -
Liu Feng,
Yu Yihua,
Zhang Junliang
Publication year - 2009
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.200901299
Subject(s) - cycloaddition , oxazines , chemistry , stereoselectivity , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry
Rapid access : A gold(I)‐catalyzed 1,3‐dipolar cycloaddition of 2‐(1‐alkynyl)‐2‐alken‐1‐ones with nitrones provides a practical, regiospecific, and stereoselective access to highly substituted fused bicyclic furo[3,4‐ d ][1,2]oxazines under mild conditions (see scheme). These fused heterobicyclic compounds can be readily converted into furans or 3,6‐dihydro‐2 H ‐1,2‐oxazines in a chemoselective fashion.