Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions

TETRAHEDRON

卷:73

Article

Radomkit, Suttipol¹  Liu, Zhenxing¹  Closs, Anna¹  Mikus, Malte S.¹  Hoveyda, Amir H.¹ 

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

关键词: Allylic substitution;    Boron;    Catalysis;    Copper;    Enantioselective synthesis;    Vicinal diboron compounds;   

DOI  :  10.1016/j.tet.2017.05.068

来源: Elsevier

【 摘 要 】

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 PCy3 or PPh3, CuCl and LiOt-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-2(pin)(2) 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. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

Free