The enantioselective synthesis of tetralin derivatives bearing a trifluoromethylated all-carbon quaternary stereocenter has been accomplished through a synthetic sequence comprising an organocatalytic β-functionalization of ortho-1-trifluoromethylvinyl-(hetero)aromatic conjugated aldehydes followed by the intramolecular nitrone 1,3-cycloaddition reaction (INCR). Both nitromethane and N-Cbz-hydroxylamine were employed as nucleophiles in the initial organocatalytic conjugate addition step, which provided the chiral information required for the subsequent diastereoselective INCR. Although diastereoselectivity was moderate, good yields and enantioselectivities were, in general, obtained. Interestingly, an inversion of the selectivity in the intramolecular cycloaddition step was observed when either nitromethane or N-Cbz-hydroxylamine was employed. This outcome was studied by means of theoretical calculations, which were in agreement with the experimental results. In addition, the ring opening of the isoxazolidine moiety furnished the corresponding fluorinated diamino alcohols in a very efficient manner.

中文翻译：

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顺序（杂）Michael反应-分子内氮环加成反应有机合成三氟甲基四氟甲基衍生物的对映体选择性催化

具有三氟甲基化的全碳四元立体中心的四氢化萘衍生物的对映选择性合成是通过合成序列完成的，该合成序列包括邻-1-三氟甲基乙烯基-（杂）芳族共轭醛的有机催化β-官能化，然后进行分子内硝酮1,3-环加成反应（INCR）。硝基甲烷和氮-Cbz-羟胺在最初的有机催化共轭加成步骤中用作亲核试剂，为后续的非对映选择性INCR提供所需的手性信息。尽管非对映选择性中等，但通常获得了良好的收率和对映选择性。有趣的是，当使用硝基甲烷或N -Cbz-羟胺时，观察到分子内环加成步骤中选择性的反转。通过理论计算研究了这一结果，该结果与实验结果相符。另外，异恶唑烷部分的开环以非常有效的方式提供了相应的氟化二氨基醇。