Highly diastereoselective nucleophilic addition of organometallic reagents to 2-pyrrolidinyl nitrones: a semiempirical approach
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Add time:07/28/2019 Source:sciencedirect.com
2-Pyrrolidinyl nitrones 1 and 2 derived from l-proline and trans-4-hydroxy-l-proline, respectively, undergo nucleophilic additions of Grignard reagents and organolithium compounds with high syn selectivity, to yield enantiomerically pure pyrrolidinyl benzyl hydroxylamines. A rationale for the observed stereoselectivity based on semiempirical calculations is presented.
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