158249-51-5

Usage

Uses

Used in Pharmaceutical Research:
(4S)-4-Butyl-2-oxazolidinone is used as a building block for the development of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of new compounds with potential therapeutic and pesticidal properties.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, (4S)-4-Butyl-2-oxazolidinone is utilized as a chiral auxiliary. This application is crucial for the synthesis of enantiomerically pure compounds, which are essential in the pharmaceutical industry to ensure the desired biological activity and minimize potential side effects.
Used in Organic Synthesis:
(4S)-4-Butyl-2-oxazolidinone serves as a valuable building block in organic synthesis, enabling the creation of a wide range of compounds with diverse properties. Its reactivity and structural features make it an essential component in the development of new chemical entities for various applications.

Upstream product

• 6920-22-5 Hexane-1,2-diol 
• 57-13-6 urea 
• 327-57-1 L-Norleucine 
• 153531-44-3 (4R)-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion

Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].

(Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols

A novel strategy for the synthesis of oxazolidin-2-ones from vicinal diols and urea is described. In this heterocycle synthesis, two different C?O and C?N bonds are sequentially formed in a domino process consisting of nucleophilic substitution and alcohol amination. The use of readily available starting materials and the good atom economy render this process environmentally benign. While this transformation is already highly chemo- and regioselective, we also developed the first asymmetric version of this method using (R)-(+)-MeO-BIPHEP as the chiral ligand.

Synthesis and Inhibitory Mechanisms of Phospholipase A2 Inhibitors

Two types of Phospholipase A2 (PLA2) inhibitor were synthesized, one of which was a terpenoid having unsaturated aldehyde, and the other was a cyclic phospholipid analog. The inhibitory mechanisms of each compound were proposed. Thus, the former may irreversibly modify an interfacial recognition site, and the latter competitively binds to the catalytic site of PLA2 with the mode similar to that of the genuine substrate.

Diastereoselective Addition of Organometallic Reagents to Imines or Hydrazones Containing 1,3-Oxathiane As a Chiral Template

The addition of organometallic reagents to imines or hydrazones containing 1,3-oxathiane as a chiral auxiliary proceeded with high diastereoselectivity and can be used as a key reaction for the preparation of chiral β-amino alcohols.