Copper(I)-Catalyzed Substitution of Propargylic Carbonates with Diboron: Selective Synthesis of Multisubstituted Allenylboronates
Copper(I)-Catalyzed Substitution of Propargylic Carbonates with Diboron: Selective Synthesis of Multisubstituted Allenylboronates
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DOI：
10.1021/ja806602h
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发表时间：
2008-11-26
影响因子：
15
通讯作者：
Sawamura, Masaya
中科院分区：
文献类型：
--
作者：
Ito, Hajime;Sasaki, Yusuke;Sawamura, Masaya
介绍了一种制备烯基硼酸盐的通用合成方法，即Cu(I)催化碳酸丙酯与二硼的反应。Cu(O-t-Bu)-Xantphos催化剂体系对制备各种烯基硼化合物、具有不同取代模式的烯基硼酸盐、具有官能团的烯基硼酸盐和轴向手性烯基硼酸盐是有效的。路易斯酸促进了醛的立体选择性加成，得到了同丙基醇，表明了新型硼烯酸酯的实用性。
A versatile synthetic method for the preparation of the allenylboronates, Cu(I)-catalyzed reaction of propargylic carbonates with a diboron, is described. A Cu(O-t-Bu)-Xantphos catalyst system was effective for the preparation of various allenylboron compounds, allenylboronates with different substitution patterns, those with functional groups, and an axially chiral one. The Lewis acid promoted stereoselective addition to aldehydes leading to homopropargylic alcohols showed the usefulness of the new allenylboronates.