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2004
Amino acids
U 0400
Novel Asymmetric Approach to Proline-Derived Spiro-β-lactams. — The title apis based on the concept of sacrificing the asymmetry at C-4 of lactams (III) and
51- 167 proach
(IV) in subsequent transformations to target lactams (VI) and (VIII). The chiral group
at the 4-position of proline acid chloride (I) directs the stereoselectivity of the reaction
with imines (II). It is found that good stereoselectivity in these Staudinger reactions is
achieved for mesyloxy derivative (I), whereas the corresponding tosyl and nosyl analogues react with less stereoselectivity. The imines give good selectivities if R1 is aromatic and R2 either aliphatic or aromatic. — (KHASANOV, A. B.; RAMIREZ-WEINHOUSE, M. M.; WEBB, T. R.; THIRUVAZHI*, M.; J. Org. Chem. 69 (2004)
17, 5766-5769; ChemBridge Res. Lab., Dep. Chem. Res., ChemBridge Corp., San
Diego, CA 92127, USA; Eng.) — Klein
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