Asymmetric Conjugate Addition of Phosphine Sulfides to α-Substituted β-Nitroacrylates Using Cinchona Alkaloid Amide Catalysts

Chiral phosphine-containing amino acids are useful motifs in pharmaceutical compounds. In this study, we developed the asymmetric conjugate addition of phosphine sulfides with α-substituted β-nitroacrylates to synthesize phosphine-containing amino acid precursors with chiral tetrasubstituted carbon centers. This method showed a wide substrate scope, and the obtained products were converted into various chiral compounds. The origin of the enantioselectivity was clarified by computational analysis.

Authors

Institutions

Publication Details

Journal
Organic Letters
Published
2024-09-20
DOI
https://doi.org/10.1021/acs.orglett.4c02643
Citations
4
Primary Topic
Organophosphorus compounds synthesis
Type
article
Field-Weighted Citation Impact
1.00
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Asymmetric Conjugate Addition of Phosphine Sulfides to α-Substituted β-Nitroacrylates Using Cinchona Alkaloid Amide Catalysts

Kazuki Fujita, Tsunayoshi Takehara, Shuichi Nakamura, Naoki Yasukawa et al.
4 citations
Organic Letters
Organophosphorus compounds synthesis
1.00
article

Asymmetric Conjugate Addition of Phosphine Sulfides to α-Substituted β-Nitroacrylates Using Cinchona Alkaloid Amide Catalysts

Kazuki Fujita, Tsunayoshi Takehara, Shuichi Nakamura, Naoki Yasukawa, Takeyuki Suzuki, Akane Iwamura, Kosei Miyake
article en
4 citations

Abstract

Chiral phosphine-containing amino acids are useful motifs in pharmaceutical compounds. In this study, we developed the asymmetric conjugate addition of phosphine sulfides with α-substituted β-nitroacrylates to synthesize phosphine-containing amino acid precursors with chiral tetrasubstituted carbon centers. This method showed a wide substrate scope, and the obtained products were converted into various chiral compounds. The origin of the enantioselectivity was clarified by computational analysis.

Organic LettersVol. 26(39)
Nagoya Institute of Technology (JP), The University of Osaka (JP)
Clean water and sanitation
Openalex Percentile: Top 27%
Organophosphorus compounds synthesis
1.00
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.