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Original Articles

Lewis acid–mediated reactions of propargyl chalcogenides with ethyl glyoxylate

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Pages 268-273 | Received 04 Jun 2015, Accepted 12 Jun 2015, Published online: 06 Feb 2016
 

GRAPHICAL ABSTRACT

ABSTRACT

The [3+2] cycloaddition reaction of mesityl propargyl sulfide with ethyl glyoxylate was found to occur by using tin(IV) chloride to give a 2,5-dihydrofuran derivative. On the other hand, when 3-silyl propargyl sulfides were used, allyl alcohols were obtained. In the case of propargyl sulfides possessing dimethyl groups at the α-position of the propargyl group, cycloaddition products were obtained even if a silyl group was present on the propargyl group. In addition, mesityl propargyl selenides also reacted with ethyl glyoxylate by using tin(IV) chloride to give the corresponding [3+2] cycloaddition products.

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