基于氢键稳定烯炔酰胺的2,3-联烯酰胺的不对称有机催化合成
Asymmetric Organocatalytic Synthesis of 2,3-Allenamides from Hydrogen-Bond-Stabilized Enynamides.
作者信息
Ma Zhi-Gang, Wei Jie-Lu, Lin Jun-Bing, Wang Guan-Jun, Zhou Jia, Chen Kai, Fan Chun-An, Zhang Shu-Yu
机构信息
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou 730000 , China.
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , Shanghai 200240 , China.
出版信息
Org Lett. 2019 Apr 5;21(7):2468-2472. doi: 10.1021/acs.orglett.9b00839. Epub 2019 Mar 25.
Asymmetric catalytic synthesis of 2,3-allenamides from hydrogen-bond-stabilized enynamides in the presence of quinine-based bifunctional squaramide organocatalysts is described. This protocol forms a variety of 2,3-allenamides in high yields and excellent stereoselectivities, in which the elaborated introduction of intramolecular H-bonds within the N, N-bidentate amide group constitutes one of the keys to this highly enantioselective transformation. The synthetic practicality of this reaction has been demonstrated by the axis-to-center chirality transfer of allenamides to furnish enantiomerically enriched building blocks.
描述了在基于奎宁的双功能方酰胺有机催化剂存在下，由氢键稳定的烯炔酰胺不对称催化合成2,3-联烯酰胺。该方法能以高产率和优异的立体选择性形成多种2,3-联烯酰胺，其中在N，N-双齿酰胺基团内精心引入分子内氢键是这种高对映选择性转化的关键之一。通过联烯酰胺的轴到手性转移以提供对映体富集的结构单元，证明了该反应的合成实用性。
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