The development of an approach toward sterically-hindered chiral 2 '-aryl-1,1 '-binaphthalenes functionalized at position 2

作者：Meskova Michaela; Putala Martin^*

来源：Tetrahedron Letters, 2011, 52(41): 5379-5383.

DOI：10.1016/j.tetlet.2011.08.046

• Binaphthyl
• Negishi cross-coupling
• Palladium
• Phosphanylation
• Suzuki cross-coupling

Several approaches were examined for the preparation of 1,1'-binaphthalene derivatives bearing sterically demanding ortho-substituted aryl at position 2' which are suitable for further functionalization at position 2. Steric hindrance of ortho-substituted aryl groups was critical for the approach through BINOL monotriflate. Among variations of cross-coupling reactions of 2,2'-dihalo-1,1'-binaphthalenes, Negishi arylation of an enantiopure 2,2'-dibromide was found to be the method of choice for regioselective and stereoconservative preparation of the target 2'-monoarylated precursor. Functionalization of the latter at position 2 was demonstrated by bromine substitution via lithiation followed by the reaction with several electrophiles.

• 出版日期2011-10-12