通过催化三组分反应实用、高效且广泛适用地合成易于区分的邻位双硼酸酯化合物。
Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.
作者信息
Radomkit Suttipol, Liu Zhenxing, Closs Anna, Mikus Malte S, Hoveyda Amir H
机构信息
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
出版信息
Tetrahedron. 2017 Aug 17;73(33):5011-5017. doi: 10.1016/j.tet.2017.05.068. Epub 2017 May 20.
A practical, efficient and broadly applicable catalytic method for synthesis of easily differentiable vicinal diboronate compounds is presented. Reactions are promoted by a combination of PCy or PPh, CuCl and LiO-Bu and may be performed with readily accessible alkenyl boronate substrates. Through the use of an alkenyl-B(pin) (pin = pinacolato) or alkenyl- B(dan) (dan = naphthalene-1,8-diaminato) starting material and commercially available (pin)B- B(dan) or B(pin) as the reagent, a range of vicinal diboronates, including those that contain a B-substituted quaternary carbon center, may be prepared in up to 91% yield and with >98% site selectivity. High enantioselectivities can be obtained (up to 96:4 er) through the use of commercially available chiral bis-phosphine ligands for reactions that afford mixed diboronate products.
本文介绍了一种实用、高效且广泛适用的催化方法，用于合成易于区分的邻位双硼酸酯化合物。反应由PCy或PPh、CuCl和LiO-Bu组合促进，并且可以使用易于获得的烯基硼酸酯底物进行。通过使用烯基-B(pin)（pin = 频哪醇硼酸酯）或烯基-B(dan)（dan = 萘-1,8-二氨基硼酸酯）起始原料以及市售的(pin)B-B(dan)或B(pin)作为试剂，可以制备一系列邻位双硼酸酯，包括那些含有B-取代季碳中心的双硼酸酯，产率高达91%，位点选择性>98%。对于生成混合双硼酸酯产物的反应，通过使用市售的手性双膦配体，可以获得高对映选择性（高达96:4 er）。
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