Synthesis of γ-amino alcohols from aldehydes, enamines, and trichlorosilane using Lewis base catalysts

DOI DOI Web Site Web Site 被引用文献6件

書誌事項

公開日
2011-01
権利情報
  • https://www.elsevier.com/tdm/userlicense/1.0/
  • https://www.elsevier.com/legal/tdmrep-license
DOI
  • 10.1016/j.tet.2010.10.075
  • 10.1002/chin.201117074
公開者
Elsevier BV

この論文をさがす

説明

The reaction of aldehydes, enamines, and trichlorosilane in the presence of a Lewis base catalyst, particularly N-methylpyrrolidinone and DMF, affords γ-amino alcohols with a high diastereoselectivity. The method consists of C–C bond formation between an aldehyde and an enamine, and a subsequent intramolecular reduction of the resulting iminium ion intermediate. In most cases, one diastereomer is exclusively generated, and we propose a transition state model for the intramolecular reduction of the iminium ion intermediate. Enamines, prepared beforehand from the corresponding ketone and amine, can be used in the reaction without purification. Furthermore, enantioselective catalysis using a chiral Lewis base catalyst is possible, although the enantioselectivity is modest. The current tandem method offers the first, concise synthetic method of γ-amino alcohols from aldehydes and enamines.

収録刊行物

  • Tetrahedron

    Tetrahedron 67 (2), 531-539, 2011-01

    Elsevier BV

被引用文献 (6)*注記

もっと見る

問題の指摘

ページトップへ