铜催化不对称 1,6-共轭加成生成的 -醌甲川与β-酮酯。
Copper-catalyzed asymmetric 1,6-conjugate addition of generated -quinone methides with β-ketoesters.
机构信息
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Department of Green Chemistry and Technology, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Taizhou College of Pharmaceutical and Chemical Engineering, 318000, Taizhou, Zhejiang, P. R. China.
出版信息
Chem Commun (Camb). 2022 Jun 8;58(46):6653-6656. doi: 10.1039/d2cc00146b.
A Cu-catalyzed asymmetric 1,6-conjugate addition of generated -quinone methides (-QMs) with β-ketoester has been developed to construct a ketoester skeleton bearing an adjacent tertiary-quaternary carbon stereocenter in good yields and high enantioselectivities. This is the first example of metal-catalyzed asymmetric transformations of the generated -QMs, avoiding using pre-synthesized -QMs requiring bulky 2,6-substitutions and highlighting a new dual catalytic activation with the chiral bis(oxazoline)-metal complex acting as a normal Lewis acid to activate the β-ketoesters and a source of Brønsted acid responsible for generating the -QMs .
一种铜催化的不对称 1,6-共轭加成反应，由 生成的 -醌甲基（-QMs）与β-酮酯反应，可以构建一个含有相邻的三级-四级碳立体中心的酮酯骨架，产率高，对映选择性好。这是首例金属催化的 生成的 -QMs 的不对称转化反应，避免了使用需要大体积 2,6-取代基的预先合成的 -QMs，并突出了一种新的双重催化活化，手性双（恶唑啉）-金属配合物作为正常的路易斯酸来活化β-酮酯，同时也是生成 -QMs 的 Brønsted 酸的来源。
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