Tartaric acid-derived chiral phosphite-type P,N-ligands: behavioural features in Pd-catalyzed asymmetric transformations

Q2 Chemistry Tetrahedron, asymmetry Pub Date : 2017-11-15 DOI:10.1016/j.tetasy.2017.09.011

Konstantin N. Gavrilov , Sergey V. Zheglov , Ilya V. Chuchelkin , Marina G. Maksimova , Ilya D. Firsin , Andrew N. Fitch , Vladimir V. Chernyshev , Alexander V. Maximychev , Alexander M. Perepukhov

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引用次数: 8

Abstract

A practical synthesis of new phosphoramidite, phosphite and diamidophosphite P,N-ligands derived from (R,R)-tartaric acid was carried out. A study of these chiral inducers showed them to provide up to 93% ee in the Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate, up to 84% ee in the Pd-catalyzed asymmetric alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate and up to 63% ee in the Pd-catalyzed desymmetrization of N,N′-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate. The effects of the structural modules, such as the nature of the phosphorus-containing ring or exocyclic substituent as well as of the nature of palladium source on the catalytic activity and enantioselectivity were investigated.

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酒石酸衍生的手性磷酸盐型P, n配体:pd催化不对称转化的行为特征

以(R,R)酒石酸为原料合成了新型磷酸亚磷酸酯、亚磷酸酯和二磷亚磷酸酯P, n配体。对这些手性诱导剂的研究表明，它们在pd催化的(E)-1,3-二苯丙烯乙酸酯的不对称烯化反应中提供高达93%的ee，在pd催化的肉桂乙酸酯与2-氧环己烷-1-羧酸乙酯的不对称烷基化反应中提供高达84%的ee，在pd催化的N,N ' -二烷基-中-环戊-4- 1,3-二醇双氨基甲酸酯的反对称反应中提供高达63%的ee。考察了含磷环或外环取代基的性质以及钯源的性质等结构模块对催化活性和对映选择性的影响。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

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0.00%

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审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.

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