Tetrahedron p. 7761 - 7770 (1996)
Update date:2022-08-05
Topics:
Falck-Pedersen, Mette Lene
Undheim, Kjell
(S,S)-α,α'-Diamino-1,4-and 1,3-benzenediacetic acids and N-Boc- and N- Fmoc-derivatives have been prepared by stereoselective syntheses. The chiral auxiliary (S)-4-benzyl-2-oxazolidinone formed bisimides with benzenediacetlyl dichlorides. The imides were lithiated at both α-sites to the carbonyl groups and azidated stereoselectively alpha to both carbonyl groups by trisyl azide to provide (S,S)-α,α'-diazidobenzenediacetic acid derivatives which were reduced to amines by Sn(II) choride or by hydrogenolysis over Pd.
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