Asymmetric Synthesis of α-Aryl Amino Acids; Aryne-Mediated Diastereoselective Arylation

Asymmetric Synthesis of α-Aryl Amino Acids; Aryne-Mediated Diastereoselective Arylation

An aryne-mediated α-arylation reaction of Schöllkopf’s bis-lactim ether is described. Arynes were generated via an ortho-lithiation approach, affording syn-arylated products in up to 94:6 dr with moderate to good yields and excellent regioselectivities. Hydrolysis provided a variety of substituted...

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Veröffentlicht in:Organic letters 2011-03, Vol.13 (5), p.1012-1015
Hauptverfasser: Jones, Elizabeth P, Jones, Peter, Barrett, Anthony G. M
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Benzene Derivatives - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:An aryne-mediated α-arylation reaction of Schöllkopf’s bis-lactim ether is described. Arynes were generated via an ortho-lithiation approach, affording syn-arylated products in up to 94:6 dr with moderate to good yields and excellent regioselectivities. Hydrolysis provided a variety of substituted arylglycines containing a range of functional groups without racemization.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1030469