Copper-Catalyzed Direct Asymmetric Aldol Reaction of Glycine Schiff Bases to Access <i>syn</i>-β-Hydroxy-α-amino Esters

This study reported a copper-catalyzed direct asymmetric aldol reaction between aldehydes and glycine Schiff bases with methyl, allyl, and <i>tert</i>-butyl esters. Additionally, this reaction afforded high yields of <i>syn</i>-β-hydroxy-α-amino esters with excellent enantio- and diastereoselectivities (93-99% ee, up to >99:1 dr). The aldol reaction accepted aromatic, linear aliphatic, and α-substituted aliphatic aldehydes.

Authors

Institutions

Publication Details

Journal
Organic Letters
Published
2024-09-10
DOI
https://doi.org/10.1021/acs.orglett.4c03085
Citations
5
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
1.25

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Copper-Catalyzed Direct Asymmetric Aldol Reaction of Glycine Schiff Bases to Access syn-β-Hydroxy-α-amino Esters

Masakatsu Shibasaki, Toshifumi Takeuchi
5 citations
Organic Letters
Asymmetric Synthesis and Catalysis
1.25
article

Copper-Catalyzed Direct Asymmetric Aldol Reaction of Glycine Schiff Bases to Access syn-β-Hydroxy-α-amino Esters

Masakatsu Shibasaki, Toshifumi Takeuchi
article en
5 citations

Abstract

This study reported a copper-catalyzed direct asymmetric aldol reaction between aldehydes and glycine Schiff bases with methyl, allyl, and <i>tert</i>-butyl esters. Additionally, this reaction afforded high yields of <i>syn</i>-β-hydroxy-α-amino esters with excellent enantio- and diastereoselectivities (93-99% ee, up to >99:1 dr). The aldol reaction accepted aromatic, linear aliphatic, and α-substituted aliphatic aldehydes.

Organic LettersVol. 26(37)
Microbial Chemistry Research Foundation (JP)
Japan Society for the Promotion of Science
Clean water and sanitation
Openalex Percentile: Top 23%
Asymmetric Synthesis and Catalysis
1.25
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.