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Pyrrolidine based chiral organocatalyst for efficient asymmetric Michael addition of cyclic ketones to β-nitrostyrenes.

Bioorganic & medicinal chemistry letters (2012-06-08)
Kamal Nain Singh, Paramjit Singh, Pushpinder Singh, Nand Lal, Sandeep Kumar Sharma
RÉSUMÉ

An efficient asymmetric Michael addition of cyclic ketones to β-nitrostyrenes using secondary diamine as an organocatalyst derived from l-proline and (R)-α-methylbenzyl amine has been described. This pyrrolidine based catalyst 1 was found to be very effective to synthesize various γ-nitrocarbonyl compounds in good yield (up to 81%) with excellent stereoselectivity (up to >99:1 dr and >99% ee).

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Sigma-Aldrich
trans-β-Nitrostyrene, 99%