Controlling the C(sp3)-C(sp2) Axial Conformatio Enantioselective Friedel Crafts-Type Alkylation of β-Naphthols with Inden-1-ones n in the

被引：23
|
作者：
Di Iorio, Nicola [1 ]
Filippini, Giacomo [1 ]
Mazzanti, Andrea [1 ]
Righi, Paolo [1 ]
Bencivenni, Giorgio [1 ]
机构：
[1] Univ Bologna, Alma Mater Studiorum, Dept Ind Chem Toso Montanari, Viale Risorgimento 4, I-40136 Bologna, Italy
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 24期
关键词：
DYNAMIC THERMODYNAMIC RESOLUTION; ATROPISOMERIC AMIDES; ASYMMETRIC-SYNTHESIS; RESTRICTED ROTATION; TETRAHEDRAL CARBON; STEREODYNAMICS; ACTIVATION; ISOMERISM; CATALYSIS;
D O I：
10.1021/acs.orglett.7b03415
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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(3))-C(sp(2)) single bond.
引用
收藏
页码：6692 / 6695
页数：4
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