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Start Over "Isamu Shiina" Journal advanced synthesis & catalysis Publisher wiley
1 results on '"Isamu Shiina"'

1. The Direct, Enantioselective, One-Pot, Three-Component, Cross-Mannich Reaction of Aldehydes: The Reason for the Higher Reactivity of Aldimineversus Aldehyde in Proline-Mediated Mannich and Aldol Reactions

Author

Yujiro Hayashi, Tadafumi Uchimaru, Isamu Shiina, Tatsuya Urushima, and Mitsuru Shoji

Subjects
chemistry.chemical_classification, Benzaldehyde, chemistry.chemical_compound, Aldimine, Nucleophile, chemistry, Aldol reaction, Organocatalysis, Electrophile, Organic chemistry, General Chemistry, Aldehyde, Mannich reaction
Abstract

In the proline-mediated Mannich and aldol reactions of propanal as a nucleophile, the aldimine prepared from benzaldehyde and p-anisidine is about 7 times more reactive than the corresponding alde- hyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic ni- trogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically veri- fied.

Published
2005
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