Direct Catalytic Enantio- and Diastereoselective Aldol Reaction of Thioamides

• Mouri Shinsuke

• Iwata Mitsutaka

• Yazaki Ryo

• Kumagai Naoya

• Shibasaki Masakatsu

Bibliographic Information

Other Title

• チオアミドのジアステレオ選択的 触媒的不斉ダイレクトアルドール反応の開発

Abstract

A direct catalytic asymmetric aldol reaction of thioamides using a soft Lewis acid/hard Bronsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF6/LiOAr is described. Exclusive enolate generation from thioacetamides through a soft-soft interaction with the soft Lewis acid allowed for a direct aldol reaction to a-nonbranched aliphatic aldehydes, which are usually susceptible to self-condensation under conventional basic conditions. A hard Lewis basic phosphine oxide has emerged as an effective additive to constitute a highly active ternary soft Lewis acid/hard Bronsted base/hard Lewis base cooperative catalyst, enabling a direct enantio- and diastereoselective aldol reaction of thiopropionamides. Divergent transformation of the thioamide functionality is an obvious merit of the present aldol methodology, allowing for a facile transformation of the aldol product into the corresponding aldehyde, ketone, amide, amine, and ketoester.

Journal

• Proceedings of the Symposium on Progress in Organic Reactions and Syntheses

  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses 37 (0), 112-112, 2011

  Division of Organic Chemistry, The Pharmaceutical Society of Japan

Keywords

• asymmetric reaction
• direct aldol
• thioamide
• cooperative catalyst
• proton transfer

Details

• CRID: 1390282680610595200
• NII Article ID: 130006996047
• DOI: 10.14895/hannou.37.0.112.0
• Text Lang: ja
• Data Source:
  • JaLC
  • CiNii Articles
• Abstract License Flag: Disallowed