Asymmetric Synthesis of (S)-2-Amino-3-(1-naphthyl)propanoic Acid via Chiral Nickel Complex. Crystal Structure, Circular Dichroism, 1H and 13C NMR Spectra of the Complex
2005 ◽
Vol 70
(9)
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pp. 1397-1410
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Keyword(s):
X Ray
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The recently published environmentally friendly preparation of a glycine synthon 2 from regeneratable chiral auxiliary BPB ((S)-N-(2-benzoylphenyl)-N'-benzylprolinamide) was used for preparative asymmetric synthesis of the non-coded amino acid 3-(1-naphthyl)alanine (1). Full assignment of 1H and 13C NMR of both intermediate complex 3 and 1 and X-ray structure determination of complex 3 were made. Cotton effects observed in circular dichroism spectrum of complex 3 are consistent with published empirical rules.