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Usage

Uses

Used in Organic Synthesis:
(4S,4'S)-4,4'-di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole is used as a key intermediate in the synthesis of various complex organic molecules. Its unique structure and stereochemistry make it a versatile building block for creating novel compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4S,4'S)-4,4'-di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole is used as a starting material for the development of new drugs. Its specific stereochemistry and functional groups can be exploited to design molecules with targeted biological activities, potentially leading to the creation of innovative therapeutic agents.
Used in Research and Development:
(4S,4'S)-4,4'-di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole is also utilized in research and development settings to study the effects of stereochemistry on molecular interactions and biological activities. Understanding these relationships can help scientists develop more effective drugs and materials with improved selectivity and potency.

Upstream product

• 599177-51-2 N,N'-bis[(1S)-1-(S)-sec-butyl-2-hydroxyethyl]ethanediamide 
• 24629-25-2 (S)-isoleucinol 

Relevant academic research and scientific papers

Asymmetric Ni-Catalyzed Radical Relayed Reductive Coupling

Alkene dicarbofunctionalizations enable the streamlined construction of aliphatic structures and have thus been the subject of intense research efforts. Despite significant progress, catalytic asymmetric variants remain scarce. Inspired by the advantages of reductive cross-coupling approaches, we present here a highly efficient asymmetric intermolecular Ni-catalyzed reductive dicarbofunctionalization of alkenes. Two distinct readily available electrophiles, namely, Csp2- and Csp3-halides, are added simultaneously across a variety of olefins (vinyl amides, vinyl boranes, vinyl phosphonates) at room temperature in a highly regio- and enantioselective manner. The reaction, devoid of sensitive organometallic reagents, takes advantage of an in situ generated chiral alkyl Ni(III)-intermediate to ensure a stereodefined outcome in the Csp3-Csp2 bond-forming reaction. An (l)-(+)-isoleucine chiral bisoxazoline ligand and the presence of coordinating sites on the alkene are key for the successful outcome in these asymmetric radical relayed reductive couplings (ARRRCs). Further, multiple transformations of the chiral amides obtained in this process showcase the potential of this new methodology for the straightforward assembly of chiral building blocks such as primary and secondary amines and oxazolines, highlighting its synthetic utility.