Z-Enolate Geometry in the Thioamide Aldol Reaction Illuminated by the 7-Azaindoline Auxiliary

Roman Pluta, Zhao Li, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article査読

1 被引用数 (Scopus)

抄録

Z or E enolate geometry is the primary determinant of diastereoselectivity in the aldol reaction. Although amide and thioamide enolates are anticipated to have predominantly the E geometry because of the intrinsic steric demand, spectroscopic confirmation of the geometry in solution has remained elusive, particularly in the realm of highly stereoselective catalytic asymmetric aldol reactions. Herein we demonstrate that the 7-azaindoline auxiliary enables direct observation of the exclusive formation of the Z-enolate of the thioamide en route to a highly syn-selective aldol reaction.

本文言語English
ページ(範囲)791-794
ページ数4
ジャーナルOrganic Letters
22
3
DOI
出版ステータスPublished - 2020 2 7
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

フィンガープリント

「Z-Enolate Geometry in the Thioamide Aldol Reaction Illuminated by the 7-Azaindoline Auxiliary」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