ChemInform Abstract: Stereoselective Mannich‐Type Reaction of an Acyclic Ketimine with a Substituted Chlorotitanium Enolate: Efficient Approach to D‐erythro‐α‐Trifluoromethyl‐β‐hydroxyaspartic Units.

Bravo, Pierfrancesco; Fustero, Santos; Guidetti, Maurizia; Volonterio, Alessandro; Zanda, Matteo

doi:10.1002/chin.200012208

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“…In 1998, Zanda and colleagues synthesized the first substituted representative of 2-trifluoromethyl azetidine-2-carboxylic acid (Scheme 80). 207 The authors performed TiCl 4 -mediated condensation between compounds 442 and 443 to obtain product 444 in 88% yield as a single isomer (Scheme 80). Reduction of the amide moiety with sodium borohydride gave alcohol 445 in 87% yield.…”

Section: Mitsunobu Reaction Ofmentioning

confidence: 99%

Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities

Mykhailiuk

2022

J. Org. Chem.

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Fluorinated prolines play an important role in peptide studies, protein engineering, medicinal chemistry, drug discovery, and agrochemistry. Since the first synthesis of 4-fluoroprolines by Gottlieb and Witkop in 1965, their popularity started to grow exponentially. For example, during the past two decades, all isomeric trifluoromethyl-substituted prolines have been synthesized. In this Perspective, chemical properties and applications of fluorinated prolines are discussed. Synthetic approaches to all known fluorine-containing prolines are also discussed and analyzed. This analysis unexpectedly revealed an unsolved problem: in strict contrast to fluoro- and trifluoromethyl-substituted prolines, the corresponding analogues with fluoromethyl and difluoromethyl groups are mostly unknown. At the end of the paper, structures of several interesting, yet unknown, fluorinated prolines are discloseda good opportunity for chemists to make them.

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Section: Mitsunobu Reaction Ofmentioning

confidence: 99%

Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities

Mykhailiuk

2022

J. Org. Chem.

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show abstract

ChemInform Abstract: Stereoselective Mannich‐Type Reaction of an Acyclic Ketimine with a Substituted Chlorotitanium Enolate: Efficient Approach to D‐erythro‐α‐Trifluoromethyl‐β‐hydroxyaspartic Units.

Cited by 1 publication

References 1 publication

Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities

Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities

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