Abstract
The Michael additions of α-toluenethiol, methylamine, and benzylamine to 4-hydroxypent-2-enoic acid lactone have been confirmed to be facile. The analogous additions of imidazole and glycine amide are much less readily accomplished and no stable Michael addition product could be detected with guanidine as the base. In the pH range 6–9, subsequent lactone ring opening reactions of the Michael addition products were observed only when methylamine (pKa 9.3) and benzylamine (pKa 10.6) were used as nucleophiles.
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