Direct Catalytic Asymmetric Vinylogous Mannich-Type and Michael Reactions of an α,β-Unsaturated γ-Butyrolactam under Dinuclear Nickel Catalysis
Direct Catalytic Asymmetric Vinylogous Mannich-Type and Michael Reactions of an α,β-Unsaturated γ-Butyrolactam under Dinuclear Nickel Catalysis
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DOI：
10.1021/ja1002636
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发表时间：
2010-03-24
影响因子：
15
通讯作者：
Shibasaki, Masakatsu
中科院分区：
文献类型：
--
作者：
Shepherd, Nicholas E.;Tanabe, Hirooki;Shibasaki, Masakatsu
描述了以α，β-不饱和伽马-丁内酰胺为给体的直接催化不对称乙烯反应。在简单的质子转移条件下，同核Ni-2-Schiff碱配合物促进了N-Boc亚胺的Ven-logy-Mannich反应和N-Boc亚胺与N-BOC亚胺的Ven-logy-Michael反应。在5：1->；30：1dr和99%ee时得到了Vinylogy Mannich加合物，在16：1->；30：1dr和93-99%ee时得到了vinylogy-mannich加合物。
Direct catalytic asymmetric vinylogous reactions of an alpha,beta-unsaturated gamma-butyrolactam as a donor are described. A homodinuclear Ni-2-Schiff base complex promoted a vinylogous Mannich-type reaction of N-Boc imines as well as a vinylogous Michael reaction to nitroalkenes selectively at the gamma-position under simple proton-transfer conditions. Vinylogous Mannich adducts were obtained in 5:1 -> 30:1 dr and 99% ee, and vinylogous Michael adducts were obtained in 16:1 -> 30:1 dr and 93-99% ee.