Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters,Angewandte Chemie International Edition

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Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2022-05-31 , DOI: 10.1002/anie.202205816
Molly E Fairchild ₁ , Adam Noble ₁ , Varinder K Aggarwal ₁

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An electrophile-induced ring contractive 1,2-metallate rearrangement of 6-membered cyclic alkenyl boronate complexes enables the synthesis of cyclopentyl boronic esters bearing two contiguous, fully substituted stereocenters with excellent levels of enantio- and diastereocontrol. The utility of our methodology is demonstrated in the asymmetric total synthesis of (+)-herbertene-1,14-diol.

中文翻译：

带有连续完全取代立构中心的环戊基硼酸酯的非对映发散合成

6 元环烯基硼酸酯配合物的亲电诱导环收缩 1,2-金属化物重排能够合成带有两个连续的、完全取代的立体中心的环戊基硼酸酯，具有优异的对映体和非对映体控制水平。我们的方法的实用性在 (+)-herbertene-1,14-二醇的不对称全合成中得到了证明。

更新日期：2022-05-31

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