立体中心
金鸡纳
对映选择合成
化学
磺胺
立体选择性
催化作用
生物碱
金鸡纳生物碱
立体化学
有机化学
组合化学
作者
Kazuki Fujita,Momona Hattori,Tsunayoshi Takehara,Takeyuki Suzuki,Shuichi Nakamura
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-04-17
卷期号:25 (16): 2835-2839
被引量:3
标识
DOI:10.1021/acs.orglett.3c00783
摘要
The enantioselective reaction of α-substituted β-nitroacrylates with oxazol-5-(4H)-ones (oxazolones) to construct consecutive tetrasubstituted stereogenic centers was accomplished. A cinchona alkaloid sulfonamide catalyst afforded products bearing vicinal chiral centers with excellent enantio- and diastereoselectivities. The obtained products were successively converted into various chiral compounds without loss of their enantiopurity. Furthermore, density functional theory (DFT) calculations were performed to elucidate the mechanism and origin of the observed stereoselectivity of the reaction.
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