Asymmetric Synthesis of C-2-Symmetric Axially Chiral Biaryls through Rhodium-Catalyzed and Alkyne-Controlled Diastereoselective Double [2+2+2] Cycloaddition

作者：Mori Ayaka; Araki Tatsuya; Miyauchi Yuta; Noguchi Keiichi; Tanaka Ken^*

来源：European Journal of Organic Chemistry, 2013, 2013(30): 6774-6778.

DOI：10.1002/ejoc.201300741

• Alkynes
• Axial chirality
• Biaryls
• Cycloaddition
• Rhodium

The asymmetric synthesis of C-2-symmetric axially chiral biaryls was achieved by the cationic rhodium(I)/1,3-bis(diphenylphosphino)propane (dppp) complex catalyzed diastereoselective double [2+2+2] cycloaddition of (R)-3-butyn-2-ol-derived tetraynes with functionalized monoynes. Interestingly, the use of propiolates afforded biaryls possessing large dihedral angles, and in contrast, the use of propargyl alcohol afforded biaryls possessing small dihedral angles.

• 出版日期2013-10