- Monothioacetalization of acetals catalyzed by dicyanoketene acetals
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A type of capto-dative olefin, dicyanoketene acetal such as dicyanoketene dimethyl acetal and ethylene acetal is introduced to be a novel type of π-acid catalyst for the monothioacetalization of acetals as well as the corresponding α,β-unsaturated systems. Particularly, the catalytic activity of dicyanoketene ethylene acetal was found to be superior to that of tetracyanoethylene and highly chemoselective in the crossover reaction of a ketone-, aldehyde-acetal, an alcohol THP-, and MOM-ether providing a ketone monothioacetal favorably.
- Miura, Tsuyoshi,Masaki, Yukio
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p. 10477 - 10486
(2007/10/02)
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- ACTIVATION AND SYNTHETIC APPLICATIONS OF THIOSTANNANES. THIOALKOXYLATION OF ACETALS
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The Sn-S bonds in thiostannanes, BunSn(SPh)4-n, are activated towards acetals in the presence of BF3*OEt2.Acetals of various aldehydes and ketones are converted into the corresponding monothioacetals under mild conditions.Employment of α-enal acetals induces Michael addition to give synthetically useful γ-alkoxyally sulfides.
- Sato, Tsuneo,Otera, Junzo,Nozaki, Hitosi
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p. 1209 - 1218
(2007/10/02)
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