The base-free anti-Markovnikov addition of secondary amides, anilides, lactams, ureas, bislactams, and carbamates to terminal alkynes is accomplished, for the first time, by a ruthenium-catalyzed reaction. Two complementary protocols provide stereoselective synthetic entries to either the E or the Z isomers (see scheme; cod=cycloocta-1,5-diene; DMAP=4-(N,N-dimethylamino)pyridine).
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Gooßen et al. (2005) studied this question.
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