Catalytic Enantioselective Aldol‐Type Reaction Using α‐Fluorinated Enolates. Issue 5 (4th April 2019)

• Record Type: Journal Article
• Authors: Gong, Yi; Yu, Jin‐Sheng; Hao, Yong‐Jia; Zhou, Ying; Zhou, Jian
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 5(2019)
• Page Start: 610
• Page End: 626
• Publication Date: 2019-04-04
• Subjects: Catalytic asymmetric -- aldol-type reaction -- α-fluorinated enolate precursors -- metal catalysis -- organocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900071
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Optically active α‐fluoroalkyl substituted alcohols are widely present in drugs and pharmaceutically active compounds. Catalytic enantioselective aldol‐type reaction using fluorinated enolates constitutes a powerful method for the synthesis of α‐fluorinated β‐hydroxy carbonyl compounds, which are versatile building blocks to access α‐fluorinated alcohols bearing different functionalities through an array of transformations based on carbonyl group. This Focus Review summarizes recent achievements of the catalytic enantioselective aldol reactions using fluorinated enolates derived from five different types of precursors, discusses in detail the limitation of each method, and outlines synthetic opportunities still present. Abstract : Catalytic enantioselective aldol‐type reaction using α‐fluorinated enolates constitutes a powerful protocol for the synthesis of optically active α‐fluoroalkyl‐substituted alcohols, which are widely present in drugs and bioactive compounds. This Review summarizes recent advances, discusses in detail the reaction mechanism and limitation of each method, and outlines synthetic opportunities still open.