Synthesis of pinacol esters of 2,3-alkadienylboronic acid via the copper(I) mediated coupling reaction of Knochel's (dialkoxyboryl)methylzinc reagents with propargylic tosylates
The reaction of propargyl tosylates (1) with (dialkoxyboryl)methyl-copper(I) reagents, prepared in situ from Knochel's (dialkoxyboryl)-methylzinc iodide (2) and CuCN · 2LiCl, produced 2,3-alkadienyl-boronates (3) in moderate yields. The reaction proceeded regioselectively to provide an SN2' substitution product without contamination by other products such as 3-alkynylboronate.
炔丙基甲苯磺酸酯(1)与由(Knochel's(dialkoxyboryl)-methylziodide(2)和CuCN·2LiCl原位制备的(dialkoxyboryl )methyl-copper(I)试剂反应生成2,3-alkadienyl-boronates(3)产量中等。反应区域选择性地进行,以提供一个S N 2'取代产物,而不受其他产物如3-炔基硼酸酯的污染。
Expanded Scope in Ethylene−Alkyne Cross-Metathesis: Coordinating Heteroatom Functionality at the Propargylic Position
作者:Jason A. Smulik、Steven T. Diver
DOI:10.1021/ol006035l
日期:2000.7.1
[GRAPHICS]The Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene-substituted ruthenium complex 1 catalyzed ethylene-alkyne cross-metathesis and was shown to tolerate free hydroxyl groups and coordinating functionality at the propargylic and homopropargylic positions, Hindered and enantiomerically enriched 1-substituted alkynes also react efficiently under the reported conditions.