Stereoselective aldol reactions of dihydroxyacetone derivatives catalyzed by chiral Zn2+ complexes

The direct aldol reaction between a protected dihydroxyacetone derivative and 4-nitrobenzaldehyde catalyzed by chiral Zn2+ complexes of 1-(n-carboxylalkyl)-7-aminoacyl-1,4,7,10-tetraazacyclododecane is reported. New Zn2+ complexes containing l-histidine and carboxylalkyl chains that mimic a class II...

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Bibliographic Details
Published inTetrahedron Vol. 75; no. 6; pp. 757 - 777
Main Authors Yasuda, Masato, Saga, Yutaka, Tokunaga, Takuya, Itoh, Susumu, Aoki, Shin
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.02.2019
Elsevier
Subjects
Aldol reaction
Asymmetric catalysis
Chemistry
Chemistry, Organic
Enzyme models
Macrocyclic ligands
Physical Sciences
Science & Technology
Zinc
Macrocyclic ligands
Aldol reaction
Enzyme models
Asymmetric catalysis
Zinc
D-PSICOSE
ASYMMETRIC-SYNTHESIS
DE-NOVO SYNTHESIS
ENOLATE FORMATION
AQUEOUS-MEDIA
NATURAL ALDOLASES
SYN-ALDOL
2-STEP SYNTHESIS
AMINO-ACID
PROTONIC ACID CATALYSTS
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Summary:The direct aldol reaction between a protected dihydroxyacetone derivative and 4-nitrobenzaldehyde catalyzed by chiral Zn2+ complexes of 1-(n-carboxylalkyl)-7-aminoacyl-1,4,7,10-tetraazacyclododecane is reported. New Zn2+ complexes containing l-histidine and carboxylalkyl chains that mimic a class II aldolase, carboxypeptidase A and a serine protease were designed and synthesized. Syn-aldol products were mainly formed by an aldol reaction of acetonide-protected dihydroxyacetone with benzaldehydes and other benzaldehydes in N-methylpyrrolidone (NMP)/alcohol (MeOH, EtOH or 2-PrOH) in good yields with a high degree of diastereo- and enantioselectivity (56%∼quant., 57∼>99% ee). Mechanistic aspect based on ESI-HRMS, elemental analysis and pH titrations of model ligands is also discussed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.12.060