Catalytic One‐Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules. Issue 10 (12th January 2016)

• Record Type: Journal Article
• Authors: Guo, Wusheng; Laserna, Victor; Rintjema, Jeroen; Kleij, Arjan W.
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 10(2016)
• Page Start: 1602
• Page End: 1607
• Publication Date: 2016-01-12
• Subjects: amines -- carbamates -- carbon dioxide -- one‐pot synthesis -- oxetanes; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500895
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Oxetanes are versatile building blocks in drug‐related synthesis to induce property‐modulating effects. Whereas related oxiranes are widely used in coupling chemistry with carbon dioxide (CO2 ) to afford value‐added commodity chemicals, oxetane/CO2 couplings remain extremely limited despite the recent advances in the synthesis of these four‐membered heterocycles. Here we report an effective one‐pot three‐component reaction (3CR) strategy for the coupling of (substituted) oxetanes, amines and CO2 to afford a variety of functionalized carbamates with excellent chemoselectivity and good yields. The process is mediated by an aluminium‐based catalyst under relatively mild conditions and the developed catalytic methodology can be applied to the formal synthesis of two pharmaceutically relevant carbamates with the 3CR being a key step. Abstract :