Publisher： John Wiley & Sons Inc
E-ISSN： 1099-0739|29|8|528-535
ISSN： 0268-2605
Source： APPLIED ORGANOMETALLIC CHEMISTRY (ELECTRONIC), Vol.29, Iss.8, 2015-08, pp. : 528-535
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Abstract
A sustainable D‐glucosamine ligand is successfully introduced into iron‐catalysed CC cross‐coupling reactions for the first time. The Fe(acac)2/D‐glucosamine·HCl/Et3N catalytic system was effective at 5 mol% loading in coupling reactions of Grignard reagents with organic bromides. Moderate to high efficiency was achieved with preserved stereochemistry when allyl (Csp3) or alkenyl (Csp2) bromides were coupled with phenylmagnesium (Csp2) or benzylmagnesium (Csp3) bromides. The catalytic system developed was also successfully applied for the novel and economic preparation of a Michael‐acceptor‐like starting material used in an alternative synthesis of the drug sitagliptin, a known blockbuster for the treatment of type II diabetes mellitus. Copyright © 2015 John Wiley & Sons, Ltd.
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