Stereoselective [1,2]-Phospha-Brook Rearrangement of CAMDOL-Derived H-Phosphonate: Synthesis of α-Trifluoromethyl Alcohols DOI
Ning Li, Qian Wu,

Yu Huang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 1, 2025

A highly efficient and stereoselective [1,2]-phospha-Brook rearrangement of fluoromethyl ketones has been achieved by utilizing a new type P-chiral H-phosphonate derived from CAMDOL, designated as CAMDOL-PHO. library 38 secondary alcohols featuring an α-trifluoromethyl or trifluoroaryl motif were afforded in up to 97% yield with 99:1 dr. Compared other known chiral auxiliaries, bicyclic CAMDOL exhibits superior induction ability due its unique center-chiral scaffold.

Язык: Английский

Umpolung Phosphorylation of Tyrosine via 1,2-Phospha-Brook Rearrangement DOI

T Fukuta,

Toshifumi Tatsumi,

Kohei Fujiyoshi

и другие.

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8827 - 8831

Опубликована: Окт. 10, 2024

Phosphorylated tyrosine is a fundamental building block of bioactive peptides and proteins. However, the chemoselective phosphorylation over other nucleophilic amino acid residues in unprotected remains significant challenge. Here we report an umpolung strategy that converts C-terminal into electrophilic spirolactone cyclohexadienone motif through hypervalent iodine oxidation, followed by 1,2-phospha-Brook rearrangement using phosphite diesters as phosphoryl donors. This reaction proceeds chemoselectively at phenol applicable to wide range peptide substrates containing various residues, including serine threonine.

Язык: Английский

Процитировано

5
Recent Developments in the [1,2]-Phospha-Brook Rearrangement Reaction DOI Open Access
Ning Li, Qian Wu,

Yu Huang

и другие.

International Journal of Molecular Sciences, Год журнала: 2025, Номер 26(7), С. 3065 - 3065

Опубликована: Март 27, 2025

The [1,2]-phospha-Brook rearrangement serves as a powerful synthetic strategy that enables efficient carbonyl umpolung through phosphoryl group migration, providing direct access to α-hydroxyphosphoryl compounds-a privileged class of synthons with broad applications in organophosphorus chemistry, medicinal and materials science. This review provides comprehensive overview recent progress methodologies, possible mechanisms, asymmetric transformations, highlighting key breakthroughs future directions this rapidly evolving field.

Язык: Английский

Процитировано

0
Stereoselective [1,2]-Phospha-Brook Rearrangement of CAMDOL-Derived H-Phosphonate: Synthesis of α-Trifluoromethyl Alcohols DOI
Ning Li, Qian Wu,

Yu Huang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 1, 2025

A highly efficient and stereoselective [1,2]-phospha-Brook rearrangement of fluoromethyl ketones has been achieved by utilizing a new type P-chiral H-phosphonate derived from CAMDOL, designated as CAMDOL-PHO. library 38 secondary alcohols featuring an α-trifluoromethyl or trifluoroaryl motif were afforded in up to 97% yield with 99:1 dr. Compared other known chiral auxiliaries, bicyclic CAMDOL exhibits superior induction ability due its unique center-chiral scaffold.

Язык: Английский

Процитировано

0