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Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Aminoalkyl)boronic Esters
Author(s) -
Ursinyova Nina,
Bedford Robin B.,
Gallagher Timothy
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501492
Subject(s) - borylation , chemistry , alkyl , catalysis , iodide , copper , organic chemistry , combinatorial chemistry , enantioselective synthesis , medicinal chemistry , aryl
Cyclic sulfamidates undergo borylation under copper‐catalyzed conditions using B 2 pin 2 to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; N ‐sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon‐centered radicals under these copper‐catalyzed conditions appears likely.