Abstract
(1R,5S)-3-Benzyl-7-(2-methylprop-1-enyl)-2-oxa-4,7-diazabicyclo[3.2.0]hept-3-en-6-one (2) is converted, probably by way of the azetinium ion (27), into a mixture of (3R,4R)-1-(2-methylprop-1-enyl)-4-methylthio-3-phenylacetamidoazetidin-2-one (7) and the (3R,4S)-isomer (17) by methanethiol in the presence of a Lewis acid. Corresponding reactions occur when the oxazoline (2) is similarly treated with ethanethiol, butane-1-thiol, butane-2-thiol, 2-methylpropane-2-thiol, prop-2-ene-1-thiol, ethane-1,2-dithiol, 2-mercaptoethyl acetate, methyl mercaptoacetate, and methyl 3-mercaptopropionate.
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More From: Journal of the Chemical Society. Perkin transactions 1
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