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2005
Amino acids
U 0400
CamTHP*OH: A Camphor-Derived δ-Lactol Auxiliary for the Effective Desymof Attached Glycinamide Residues. Asymmetric Synthesis of α-Ami12- 201 metrization
no Carbonyl Compounds. — A new δ-lactol title compound is designed and tested as
a stereocontrolling element in the enolate chemistry of attached glycinamide residues.
Good to excellent diastereocontrol is observed with a wide range of alkyl halides. Acid
hydrolysis affords the enantioenriched N-Cbz-protected amino acid dimethyl amides.
They are suitable substrates for further modification as is shown for (XI) which reacts
with Grignard or organolithium reagents without loss of stereochemical integrity. —
(DIXON*, D. J.; HORAN, R. A. J.; MONCK, N. J. T.; Org. Lett. 6 (2004) 24,
4423-4426; Dep. Chem., Univ. Manchester, Manchester M13 9PL, UK; Eng.) —
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