The high-pressure [4+2]cycloaddition of 1-methoxybuta-1,3-diene to the GLYCOLALDEHYDE (cas 141-46-8)-derived heterodienophiles, catalyzed by chiral metallosalen complexes
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Add time:09/30/2019 Source:infona.pl
A high-pressure (ca. 10kbar) reaction of 1-methoxybuta-1,3-diene 1 with variously O-protected glycolaldehydes 2, catalyzed by the chiral (salen)Cr(III)Cl 4a–d and 5 or (salen)Co(II) 6a–f and 7 complexes, has been studied. The best results were obtained for tert-butyldimethylsilyloxyacetaldehyde 2a. The reaction afforded, in good yield (up to 90%) and with very good diastereoselectivity (up to 92%) and enantioselectivity (up to 93% ee), the [4+2]cycloadducts 3a, which are compounds of significant synthetic interest. The stereochemical model of the cycloaddition reaction is discussed.
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