γ‐Pyronecarbaldehyde‐Based Practical Asymmetric Catalytic Synthesis of Chiral 2,4‐Dihydroxycarboxylic Acids andα‐Hydroxy‐γ‐lactones

γ‐Pyronecarbaldehyde‐Based Practical Asymmetric Catalytic Synthesis of Chiral 2,4‐Dihydroxycarboxylic Acids andα‐Hydroxy‐γ‐lactones Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2022, Volume: 364, Number: 18, Pages: 3245-3262 Pages count : 18 DOI: 10.1002/adsc.202200859

Authors

Smirnov Maxim ^1,2 , Kucherenko Alexander ² , Gridnev Ilya ² , Korlyukov Alexander Alexandrovich ³ , Zlotin Sergei ²

Affiliations

1	M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1-3, 119991 Moscow, Russian Federation
2	N D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences RUSSIAN FEDERATION

Biomass derived γ-pyrone-2-carbaldehydes were proposed as robust heterocyclic platform for carrying out organocatalytic asymmetric cross-aldol reactions with various aldehydes and ketones in high yield with excellent diastereoselectivity and enantioselectivity. Origins of efficient stereoinduction were revealed by quantum-chemical calculations of four possible transition states. The products were converted to synthetically useful chiral 2,4-dihydroxy carboxylic acid derivatives via protection/deprotection and RuIII-catalyzed oxidative fragmentation steps without racemization of stereogenic centers. The developed approach was applied for asymmetric synthesis of chiral pantolactones, valuable precursors of biologically active substances and natural products, and for synthesis of Dexpanthenol, a medication used for treating defects in the barrier function of skin.

Smirnov M. , Kucherenko A. , Gridnev I. , Korlyukov A.A. , Zlotin S.
γ‐Pyronecarbaldehyde‐Based Practical Asymmetric Catalytic Synthesis of Chiral 2,4‐Dihydroxycarboxylic Acids andα‐Hydroxy‐γ‐lactones
Advanced Synthesis & Catalysis. 2022. V.364. N18. P.3245-3262. DOI: 10.1002/adsc.202200859 WOS Scopus OpenAlex

Web of science:	WOS:000847928500001
Scopus:	2-s2.0-85137213976
OpenAlex:	W4293830004

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