Novel Asymmetric Approach to Proline-Derived Spiro-β-lactams
- 21 July 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (17) , 5766-5769
- https://doi.org/10.1021/jo049430o
Abstract
We describe a novel asymmetric approach using Staudinger chemistry to proline-derived spiro-β-lactams. A chiral group at C-4 of the acid chloride of proline directs the stereoselectivity of Staudinger chemistry and later is sacrificed to obtain optically active 5.4-spiro-β-lactams. The scope, limitations, and mechanistic rationale for the observed results of Staudinger Chemistry of the acid chloride of 4-alkyl(aryl)sulfonyloxy-l-proline with imines are also discussed.Keywords
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