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Gold(I)-catalysed [3+3] cycloaddition of propargyl acetals and nitrones.
- Source :
-
Tetrahedron . Jun2016, Vol. 72 Issue 23, p3270-3276. 7p. - Publication Year :
- 2016
-
Abstract
- In our series of investigations to expand the understanding of the gold(I) catalysis chemistry of propargyl acetals, a gold(I) catalysed [3+3] cycloaddition reaction of propargyl acetals with nitrones has been studied. A series of 5-methoxy-3,6-dihydro-2 H -1,2-oxazine products with two stereogenic centres were obtained in a cis -stereoselective manner. The formal [3+3] cycloaddition reaction is supposed to go through O-nucleophilic attack of the nitrone on the C 1 position of the gold complex generated from propargyl acetal followed by a final ring closure. An alternative C3 oxidation by nitrone affords aldehyde products and represents a competing pathway. The chemoselectivity of the cycloaddition reaction is discussed in order to demonstrate the potential and limitations of the reaction. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 72
- Issue :
- 23
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 115286322
- Full Text :
- https://doi.org/10.1016/j.tet.2016.04.058