Stereoselective Synthesis of α-Fluoro Carboxylic Acids by Ireland-Claisen Rearrangement.
Org Lett
; 25(33): 6167-6171, 2023 Aug 25.
Article
em En
| MEDLINE
| ID: mdl-37590527
ABSTRACT
Stereoselective synthesis of α-fluoro carboxylic acids by the Ireland-Claisen rearrangement can provide a straightforward approach to this class of compounds. We report a systematic investigation of base-dependent stereocontrol in the Ireland-Claisen rearrangement of α-fluoro esters. For substrates with various substitution patterns, the use of KN(SiMe3)2 in toluene afforded rearrangement products corresponding to the (Z)-enolate intermediate with a practically useful diastereoselectivity and yield. In contrast, lower yields and diastereoselectivity were consistently observed with the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).
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MEDLINE
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article