控制β-萘酚与茚满-1-酮的对映选择性 Friedel-Crafts 型烷基化反应中的 C(sp)-C(sp) 轴向构象。
Controlling the C(sp)-C(sp) Axial Conformation in the Enantioselective Friedel-Crafts-Type Alkylation of β-Naphthols with Inden-1-ones.
机构信息
Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna , Viale del Risorgimento 4, 40136 Bologna, Italy.
出版信息
Org Lett. 2017 Dec 15;19(24):6692-6695. doi: 10.1021/acs.orglett.7b03415. Epub 2017 Dec 4.
The Friedel-Crafts-type reaction between properly functionalized inden-1-ones and 2-naphthols generates a hindered single bond which displays a unique preference for an antiperiplanar conformational diastereoisomer. The steric hindrance and the presence of an enantioenriched stereogenic center control the distribution of the two diastereomeric conformers at equilibrium and increase the energy for the rotation of the C(sp)-C(sp) single bond.
吲哚-1-酮与 2-萘酚的傅克型反应生成受阻单键，对反式稠合的非对映异构体表现出独特的偏好。空间位阻和手性中心的存在控制了平衡时两种非对映异构体构象的分布，并增加了 C(sp)-C(sp)单键旋转的能量。
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