手性富集的 α-硼代锌试剂通过镍催化的乙烯基硼酸酯的碳锌化反应得到。
Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters.
机构信息
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
出版信息
J Am Chem Soc. 2021 Sep 8;143(35):14189-14195. doi: 10.1021/jacs.1c05274. Epub 2021 Aug 23.
Abstract
In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.
摘要
本文描述了通过催化对映选择性碳锌化反应合成对映体富集、构型稳定的有机锌试剂。该过程提供了对映体富集的α-硼代锌中间体，这些中间体被证明可以进行立体特异性反应，生成对映体富集的次级硼酸酯产物。该方法还对中间α-硼代锌试剂的性质进行了探究，并通过应用于（-）-阿朴啡和（-）-肠内酯的合成来证明产物的合成实用性。
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