TY - JOUR
T1 - Fluoride Anion Catalyzed Mukaiyama-Aldol Reaction
T2 - Rapid Access to α-Fluoro-β-hydroxy Esters
AU - Zong, Xinlong
AU - Liu, Shuanglei
AU - Zhang, Zhenguo
AU - Ji, Liang
AU - Zhang, Ting
AU - Jia, Zhenhua
AU - Loh, Teck Peng
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/5/20
Y1 - 2022/5/20
N2 - The Mukaiyama-Aldol reaction is probably one of the most efficient strategies to prepare synthetically useful β-hydroxy carbonyl compounds. However, only several reported methods were concerned with the accesses to α-fluoro-β-hydroxy esters. Herein, we report a protocol for a fluoride anion-mediated Mukaiyama aldol reaction with low catalytic loading in a short reaction time to incorporate fluorine at the α position into β-hydroxy esters. The method shows good functional-group tolerance and scale-up potential, moreover, is applicable to the late-stage modification of natural products and small molecular drugs.
AB - The Mukaiyama-Aldol reaction is probably one of the most efficient strategies to prepare synthetically useful β-hydroxy carbonyl compounds. However, only several reported methods were concerned with the accesses to α-fluoro-β-hydroxy esters. Herein, we report a protocol for a fluoride anion-mediated Mukaiyama aldol reaction with low catalytic loading in a short reaction time to incorporate fluorine at the α position into β-hydroxy esters. The method shows good functional-group tolerance and scale-up potential, moreover, is applicable to the late-stage modification of natural products and small molecular drugs.
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U2 - 10.1021/acs.joc.2c00240
DO - 10.1021/acs.joc.2c00240
M3 - Article
AN - SCOPUS:85129270177
SN - 0022-3263
VL - 87
SP - 6918
EP - 6926
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -