Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15257-15261. doi: 10.1002/anie.201707125. Epub 2017 Oct 25.
Acylboronate esters/trifluoroborates represent an elusive class of boronates that are of increasing interest for both fundamental study as well as applications at the interface of chemistry and biology. Their preparation has been limited by the use of strongly basic anions, often introduced in multistep reactions. Herein, we demonstrate the facile preparation of acylboronate N-methyliminodiacetyl (MIDA) esters from alkenyl-2-boronate esters through mild dihydroxylation and meta-periodate cleavage. Given the well-known functional-group tolerance of this mild reaction sequence and the availability of alkenyl-2-boronates, this method should greatly increase access to acylboronate MIDA esters.
酰基硼酸酯/三氟硼酸酯是一类难以捉摸的硼酸酯，它们在基础研究以及化学和生物学界面的应用中引起了越来越多的兴趣。它们的制备受到强碱阴离子的限制，通常通过多步反应引入。在此，我们通过温和的二羟基化和间过碘酸盐裂解，展示了从烯基-2-硼酸酯轻松制备酰基硼酸 N-甲基亚氨基二乙酸酯（MIDA）酯。鉴于该温和反应序列的众所周知的官能团耐受性以及烯基-2-硼酸酯的可用性，该方法应该大大增加酰基硼酸 MIDA 酯的获得途径。
