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Beilstein J. Org. Chem. 2011, 7, 1570–1576, doi:10.3762/bjoc.7.185
Graphical Abstract
Scheme 1: 3-Component coupling reactions of arynes. E+ = electrophile.
Scheme 2: Aryne mediated α-arylation of amino acids. DMG = directed metallation group. BHT = 2,6-di-tert-buty...
Scheme 3: Proposed mechanism of α-arylation.
Scheme 4: Proposed extension of the methodology to synthesize quaternary adducts.
Scheme 5: Formation of α-methyl, α-aryl Schöllkopf adduct.
Figure 1: NOESY correlation observed for 6a.
Figure 2: X-ray crystal structure of 6b.
Figure 3: Transition state analysis to explain the lack of diastereoselectivity at C-2.
Scheme 6: Formation of quaternary adducts.
Scheme 7: Hydrolysis of quaternary adducts.
Scheme 8: Hydrolysis to amino acids.
Scheme 9: Hydrolysis of analogue 6j.
Scheme 10: Epimerization at C-3 of 6g.