Iminophenol Ligands Derived from Chiral Regioisomeric Hydroxy[2.2]paracyclophane-carbaldehydes: the Influence of the Substitution Pattern on Asymmetric Induction†
Iminophenol Ligands Derived from Chiral Regioisomeric Hydroxy[2.2]paracyclophane-carbaldehydes: the Influence of the Substitution Pattern on Asymmetric Induction†
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手性区域异构羟基[2.2]对环芳甲醛衍生的亚氨基酚配体：取代模式对不对称诱导的影响†
DOI：
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发表时间：
2008
期刊：
影响因子：
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通讯作者：
H. Hopf
中科院分区：
文献类型：
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作者：
D. Antonov;V. Rozenberg;T. Danilova;Z. Starikova;H. Hopf
用α-苯乙胺对映体合成了平面手性12-羟基对环番-4-甲醛(3，伪FHPC)，并通过其席夫碱9拆分。用X-射线衍射法测定了3个对映体的绝对构型。合成了具有邻位、拟宝石和拟邻位排列的环番亚氨基苯酚的代表化合物7-21，并研究了它们对二乙基锌与苯甲醛的不对称加成反应的催化作用，得到了高达97 %ee的醇类化合物。(Wiley-VCH Verlag GmbH&Co.KGaA，69451温海姆，德国，2008年)
The planar-chiral 12-hydroxy[2.2]paracyclophane-4-carbaldehyde (3, pseudo-FHPC) was synthesized and resolved via its Schiff bases 9 using the enantiomers of α-phenylethylamine. The absolute configurations of the enantiomers of 3 were determined by X-ray diffraction. Derivatives 7–21, representatives of cyclophane-derived iminophenols with ortho, pseudo-gem and pseudo-ortho arrangement of the functional groups, were prepared and studied as catalysts for the enantioselective addition of diethylzinc to benzaldehyde affording the expected alcohols in up to 97 % ee. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)