Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones
Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones
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DOI：
10.1248/cpb.c17-00545
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发表时间：
2018-03-01
影响因子：
1.7
通讯作者：
Kanai, Motomu
中科院分区：
文献类型：
--
作者：
Ishizawa, Kouhei;Nagai, Hideoki;Kanai, Motomu
研究了三氟甲基酮催化羧酸选择性羟醛缩合反应。硼催化剂和羧酸之间的可逆和选择性共价键形成是实现简单羧酸的前所未有的催化羟醛缩合反应的关键。该反应进行化学选择性的羧酸的a-位置，甚至在酮，酯，或酰胺官能团的存在下，在供体基板。的化学选择性是有益的生物相关化合物的后期衍生化，如吲哚美辛和三乙酰胆酸的转化所证明的。
A catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction proceeded chemoselectively at the a-position of carboxylic acid even in the presence of ketone, ester, or amide functional groups in the donor substrates. The chemoselectivity is beneficial for late-stage derivatizations of biologically relevant compounds, as demonstrated by the conversion of indomethacin and triacetylcholic acid.