Functionalized chiral 4-nitromethyl-chromans as drug intermediates were achieved for the first time through sequential combination of Michael and acetalization reactions on 2-(2-nitro-vinyl)-phenols with acetone and alcohols in the presence of a catalytic amount of 9-amino-9-deoxyepiquinine and Ph(2)CHCO(2)H followed by p-TSA.

β-Lithiooxyphosphonium ylides, made in situ from an aldehyde and methylenetriphenylphosphorane, react with a second aldehyde to form E-allylic alcohols. α-Branching and α,β-unsaturation in the second aldehyde, together with the lack of further substitution on the phosphorane carbon play important roles in selectivity. A range of these aldehydes, in addition to aromatic aldehydes as the second a...

The first example of 'spontaneous resolution by crystallization' in allene chemistry, by means of crystal structures and solid state CD spectra of the R and S enantiomers, is presented. These allenes are prepared by the simple reaction of Ph2PCl with o-nitro functionalized propargyl alcohols.

Graphite oxide as a heterogeneous and recyclable solid acid catalyzed a simple and efficient method for the synthesis of β -amino alcohols by ring opening of epoxides with amines. This method is effective with various aromatic and aliphatic amines under solvent-free conditions. The corresponding β -amino alcohols are obtained in high yields (56%–95%) and short reaction times (15–30 min) with hi...

Enantioseparation of amino acid analogues racemic β-amino alcohols has hitherto been thought impossible without prior derivatization. Method developers of chromatographic enantioseparation often face detection challenge due to low ultraviolet (UV) absorbance of these molecules. A new chiral derivatizing reagent, benzimidazole-(S)-naproxen amide, was synthesized to provide UV detectable chiral m...

A one-pot synthesis of new variously substituted γ-chloro-γ, β-allylic carbamates have been carried out starting from β-chloro-α, β-unsaturated aldehydes. The and the corresponding intermediates, alcohols, were fully characterized by (1H 13C) NMR, IR HRMS spectroscopic techniques. crystal structures two allylic carbamates, established single-crystal X-ray diffraction.

The efficiency of direct conversion of tertiary alcohols bearing a β-hydrogen atom to vicinal halohydrins-chlorohydrins and bromohydrins-under green reaction conditions was tested preliminarily on model tertiary benzyl alcohols. Tertiary alcohols were successfully directly halogenated to vicinal halohydrins with N-halosuccinimide in aqueous media. The efficiency of the reaction in water was sig...