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Enantioselective catalytic addition of nitroesters to N-carboalkyloxy imines: a route to quaternary stereocenters

✍ Scribed by Alessandra Puglisi; Laura Raimondi; Maurizio Benaglia; Martina Bonsignore; Sergio Rossi

Book ID: 104096614
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 308 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.05.036

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✦ Synopsis

A readily available, low cost bifunctional organic catalyst promoted the addition of nitroesters to imines; in the reaction between 2-nitropropionates and N-Boc protected aldehyde-imines the product bearing a new quaternary stereocenter was obtained in up to 81% ee. The positively charged catalyst was postulated to control the attack of the enolic form of nitroester to imine through a hydrogen bonding network.

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