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Catalytic One‐Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules
Author(s) -
Guo Wusheng,
Laserna Victor,
Rintjema Jeroen,
Kleij Arjan W.
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500895
Subject(s) - oxetane , chemistry , chemoselectivity , carbamate , catalysis , combinatorial chemistry , formal synthesis , organic chemistry , commodity chemicals
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 (CO 2 ) to afford value‐added commodity chemicals, oxetane/CO 2 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 CO 2 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.