Tetrahedron

Secondary–secondary diamine catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes

SV Pansare, RL Kirby

文献索引：Pansare, Sunil V.; Kirby, Raie Lene Tetrahedron, 2009 , vol. 65, # 23 p. 4557 - 4561

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被引用次数: 23

摘要

Secondary–secondary diamines derived from S-proline are efficient catalysts for the ketone– nitroalkene Michael addition reaction. The stereoselectivity of the Michael addition is dependant on the pKa of the N-substituted aminomethyl pendant in these diamines. N′- Aryl aminomethyl pyrrolidines provide γ-nitroketones with moderate to good enantiomeric excess (65–92%). Removal of the hydrogen-bond donor group by N-methylation results in ...