One-Pot Preparation of Stable Organoboronate Reagents for the Functionalization of Unsaturated Four- and Five-Membered Carbo- and Heterocycles

One-Pot Preparation of Stable Organoboronate Reagents for the Functionalization of Unsaturated Four- and Five-Membered Carbo- and Heterocycles
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用于不饱和四元和五元碳环和杂环官能化的稳定有机硼酸酯试剂的一锅法制备

DOI:
10.1055/s-0036-1592004
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发表时间:
2018
期刊:
Synthesis
影响因子:
--
通讯作者:
D. Didier
D. Didier
中科院分区:
--
文献类型:
--
作者:
A. N. Baumann;M. Eisold;A. Music;D. Didier

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将有机硼酸酯的简便制备与其卓越的稳定性和官能团耐受性相结合,可以直接合成四元和五元碳环和杂环。虽然大多数策略依赖于硼酸作为分离中间体的异位制备,但我们证明敏感有机金属与硼醇盐的原位金属转移可以导致此类物质在室温下高度稳定。通过这些序列实现了不饱和应变结构库的相当大的扩展,扩展了这种不寻常构建块的潜在适用性。
Combining a facile preparation of organoboronates with their remarkable stability and functional group tolerance allows for the straightforward synthesis of four- and five-membered carbo- and heterocycles. While most strategies rely on the ex situ preparation of boronic acids as isolated intermediates, we demonstrate that in situ transmetalation of sensitive organometallics with boron alkoxides can lead to great stabilization of such species at room temperature. A considerable extension of the library of unsaturated strained structures is achieved through these sequences, expanding the potential applicability of such unusual building blocks.
DOI: 10.1021/acs.orglett.7b02847
发表时间: 2017-10-20
期刊: ORGANIC LETTERS
影响因子: 5.2
作者:
Baumann, Andreas N.;Eisold, Michael;Didier, Dorian
通讯作者: Didier, Dorian
DOI: 10.1021/jo00239a055
发表时间: 1988
影响因子: 3.6
作者:
B. Trost;G. Tometzki
通讯作者: G. Tometzki