The direct, enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes: The reason for the higher reactivity of aldimine versus aldehyde in proline-mediated Mannich and aldol reactions

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

研究成果: Article査読

43 被引用数 (Scopus)

抄録

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 aldehyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic nitrogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically verified.

本文言語English
ページ(範囲)1595-1604
ページ数10
ジャーナルAdvanced Synthesis and Catalysis
347
11-13
DOI
出版ステータスPublished - 2005 10

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

フィンガープリント 「The direct, enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes: The reason for the higher reactivity of aldimine versus aldehyde in proline-mediated Mannich and aldol reactions」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル