Construction of three contiguous stereocenters through amine-catalyzed asymmetric aldol reactions

Three contiguous stereocenters were constructed by an amino acid-catalyzed asymmetric aldol reaction of α-siloxyketones with racemizable α-haloaldehydes via dynamic kinetic resolution. One-pot catalytic asymmetric synthesis of the highly functionalized products could also be accomplished by the α-br...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 59; no. 54; pp. 8424 - 8427
Main Authors Hikawa, Ryoga, Shimogaki, Mio, Kano, Taichi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.07.2023
Royal Society of Chemistry
Subjects
Aldehydes
Amino acids
Asymmetry
Bromination
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALPHA-CHLORINATION
DE-NOVO SYNTHESIS
BENZOYLOXYLATION
ALDEHYDES
RACEMIZATION
FLUORINATION
CORNFORTH
DYNAMIC KINETIC RESOLUTION
TRANSFORMATIONS
CARBASUGARS
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Summary:Three contiguous stereocenters were constructed by an amino acid-catalyzed asymmetric aldol reaction of α-siloxyketones with racemizable α-haloaldehydes via dynamic kinetic resolution. One-pot catalytic asymmetric synthesis of the highly functionalized products could also be accomplished by the α-bromination of simple aldehydes and the subsequent asymmetric aldol reaction. Three contiguous stereocenters were constructed by an amino acid-catalyzed asymmetric aldol reaction of α-siloxyketones with racemizable α-haloaldehydes via dynamic kinetic resolution.
Bibliography:Electronic supplementary information (ESI) available. CCDC
https://doi.org/10.1039/d3cc01606d
For ESI and crystallographic data in CIF or other electronic format see DOI
2189663
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc01606d