手性醇取代γ-苄氧基乙烯基脲的反选择性醛醇反应及3-苄氧基-4-羟基烷烃-2-酮的合成

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-11-15 DOI:10.1016/j.tetasy.2017.10.003

Yu-Jang Li , Chuan-Chung Chung , Pin-Zu Chen

引用次数: 0

摘要

描述了手性醇取代γ-苯氧基乙烯基聚氨酯的反选择性醛醇反应。用(1S,2R,4R)-1-(羟基二苯基甲基)-7,7-二甲基双环[2,2,1]-庚烷-2-醇作为手性助剂在乙烯基聚氨酯烯酸酯醛醇反应中获得了产率高、对映选择性中等至优异的抗产物。将主要的抗乙烯酯内酯转化为3-苯氧基-4-羟基烷烃-2-酮，收率较高。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

anti-Selective aldol reactions of chiral alcohol substituted γ-benzyloxyl vinylogous urethanes and the synthesis of 3-benzyloxyl-4-hydroxylalkan-2-ones

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anti-Selective aldol reactions of chiral alcohol substituted γ-benzyloxyl vinylogous urethanes and the synthesis of 3-benzyloxyl-4-hydroxylalkan-2-ones

The anti-selective aldol reaction of chiral alcohol-substituted γ-benzyloxy vinylogous urethanes is described. The use of (1S,2R,4R)-1-(hydroxydiphenylmethyl)-7,7-dimethylbicyclo[2,2,1]-heptan-2-ol as a chiral auxiliary in the aldol reaction of a vinylogous urethane enolate was found to provide anti-products in good yields with moderate to excellent enantioselectivities. The major anti-vinylogous urethane lactones were transformed into 3-benzyloxyl-4-hydroxylalkan-2-ones in good yields.

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

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.