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2005
Carboxylic amides
Q 0490
Stereoselective Synthesis of Tetra-Substituted Olefins via Addition of Zinc Enoto Unactivated Alkynes. — A new alkylidenation reaction of active methylene
14- 090 lates
compounds allows the synthesis of fully substituted olefins in high yields and good
Z-stereoselectivity. Key step is the facile intermolecular addition reaction of a metal
enolate to a nonactivated alkyne, which takes place with a stoichiometric or catalytic
amount of Et2Zn under basic conditions. The catalytic reaction is possible for the aromatic but not for the aliphatic alkynes. The catalytic reactions show stereoselectivity
which is either comparable to or higher than the stoichiometric reactions. —
(NAKAMURA*, M.; FUJIMOTO, T.; ENDO, K.; NAKAMURA, E.; Org. Lett. 6
(2004) 26, 4837-4840; PRESTO, Japan Sci. Technol. Agency, Saitama 332, Japan;
Eng.) — Steudel
2005
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