کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5213236 | 1383150 | 2016 | 7 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Gold(I)-catalysed [3+3] cycloaddition of propargyl acetals and nitrones Gold(I)-catalysed [3+3] cycloaddition of propargyl acetals and nitrones](/preview/png/5213236.png)
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-2H-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 C1 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.
Journal: Tetrahedron - Volume 72, Issue 23, 9 June 2016, Pages 3270-3276