Chiral Phosphoric Acid-Catalyzed Hydrolytic Parallel Kinetic Resolution of Racemic Epoxides and Activated Alcohols

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 18, 2025

We report a chiral phosphoric acid-catalyzed hydrolytic parallel kinetic resolution (HPKR) of racemic epoxides and activated alcohols. Using an acyloxy-assisted activation strategy, this method enables the highly stereocontrolled hydrolysis under mild conditions. A wide range aryl-substituted secondary alcohols were effectively transformed, providing corresponding with combined yields up to 99% enantiomeric ratios exceeding 99:1.

Language: Английский

Structure Confirmation of Quinazolinone and Hydroindole Using Residual Dipolar Couplings From Polyarylisocyanide Liquid Crystal

Magnetic Resonance in Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 6, 2025

ABSTRACT Determining the constitution and configuration is a critical step in characterizing structure of small molecules. In addition to classical nuclear magnetic resonance (NMR) method conducted isotropic solutions, emerging anisotropic NMR parameters such as residual dipolar couplings (RDCs) were also employed clarify structures organic These RDCs not only confirmed that unexpectedly synthesized product was quinazolinone but validated relative diastereoisomeric hydroindole polyarylisocyanide lyotropic liquid crystalline solution through induction anisotropy. Singular value decomposition (SVD) fit experimental RDC data against low‐energy conformational sets an unexpected synthetic product, which calculated using density functional theory (DFT). This analysis aimed identify correct molecular connection sites. Furthermore, applied determine between two possible diastereoisomers.

Language: Английский

Regiodivergent Desymmetrization of meso-4,5-Epoxycyclohex-1-ene

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

Herein, we report a regiodivergent desymmetrization of meso-4,5-epoxycyclohex-1-ene, which results in the formation two enantioenriched structural isomers with high enantioselectivity from single compound using chiral catalyst.

Language: Английский