Diastereoselectivity in the Addition of Allylzinc Reagents to delta-Alkoxy-gamma, delta-disubstituted Alkenyllithium Compounds

Nicolas Bernard; Fabrice Chemla; Franck Ferreira; Naouel Mostefai; Jean-F.Normant

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Diastereoselectivity in the Addition of Allylzinc Reagents to delta-Alkoxy-gamma, delta-disubstituted Alkenyllithium Compounds

机译：在烯丙基锌试剂与δ-烷氧基-γ，δ-二取代的烯基锂化合物加成中的非对映选择性

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The carbometalation reaction of allyl- and crotylzinc bromide with metalated disubstituted homoallylic ethers gives tri-or tetrasubstituted 5-hexenyl ethers with excellent control of the diastereoselectivity. The stereochemistry of this reaction is discussed and has been attributed to an early transition state with chelation to the oxygen atom in the energetically favored conformer as the stereodetermining step.

机译：烯丙基和巴豆基锌溴化物与金属化的二取代的均烯丙基醚的碳金属化反应可得到三或四取代的5-己烯基醚，对非对映选择性的控制极好。讨论了该反应的立体化学，并将其归因于在立体确定步骤中在能量有利的构象异构体中与氧原子螯合的早期过渡态。

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《Chemistry: A European journal》 |2002年第14期|共9页
作者
Nicolas Bernard; Fabrice Chemla; Franck Ferreira; Naouel Mostefai; Jean-F.Normant;
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正文语种 eng
中图分类化学;应用化学;
关键词
carbometalation; conformation analysis; diastereoselectivity; metalacycles; zinc;

机译：碳金属化;形态分析;非对映选择性;金属环;锌;

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1. Diastereoselectivity in the Addition of Allylzinc Reagents to delta-Alkoxy-gamma, delta-disubstituted Alkenyllithium Compounds [J] . Nicolas Bernard, Fabrice Chemla, Franck Ferreira, Chemistry: A European journal . 2002,第14期

机译：在烯丙基锌试剂与δ-烷氧基-γ，δ-二取代的烯基锂化合物加成中的非对映选择性
2. Synthesis of Enantiopure 1-Aryl-l-butylamines and l-Aryl-3-butenylamines by Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (R)-Phenylglycine Amide [J] . Jan Dalmolen, Marcel van der Sluis, Jose W.Nieuwenhuijzen, European journal of organic chemistry . 2004,第7期

机译：通过烯丙基溴化锌非对映选择性加成衍生自（R）-苯基甘氨酸酰胺的亚胺合成对映体纯的1-芳基-1-丁胺和1-芳基-3-丁烯基胺
3. Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (R)-Phenylglycine Amide [J] . Marcel van der Sluis, Jan Dalmolen, Ben de Lange, Organic letters . 2001,第24期

机译：非对映选择性将烯丙基溴化锌添加到衍生自（R）-苯基甘氨酸酰胺的亚胺上
4. Diastereoselective Cobalt-Catalysed Alkylative Aldol Cyclisations using Trialkylaluminium Reagents [C] . Mairi E. Rudkin, Pekka M. Joensuu, Hon Wai Lam European Symposium on Organic Chemistry . 2009

机译：使用三烷基铝试剂的非对映选择性钴催化的烷基化醛醇环法
5. Part A. Diastereoselective synthesis of protected secondary amines via reduction /alkylation or deprotonation /alkylation of N-diphenylphosphinylimines. Part B. Synthesis of secondary amines via 1,2-addition of organometallic reagents to N-diphenylphosphinylimines and subsequent alkylation [D] . Shin, Hyunshun 2001

机译：A部分：通过N-二苯基膦亚胺的还原/烷基化或去质子化/烷基化的非对映选择性合成保护的仲胺。 B部分：通过将有机金属试剂1,2-加成到N-二苯基膦亚胺和随后的烷基化反应来合成仲胺
6. Diastereoselective Additions of Allylmetal Reagents to Free and Protected syn-αβ-Dihydroxyketones Enable Efficient Synthetic Routes to Methyl Trioxacarcinoside A [O] . Daniel J. Smaltz, Jakub Švenda, Andrew G. Myers -1

机译：allylmetal试剂与不含非对映选择性增加和受保护的sYN-αβ-Dihydroxyketones实现高效合成路线甲基Trioxacarcinoside一个
7. Synthesis of Functionalized Heterocycles Using Magnesium and Zinc Reagents. Diastereoselective Addition of Allylic Aluminum Reagents to Carbonyl Compounds. Preparation and Application of Aromatic and Benzylic Manganese Reagents [O] . Peng Zhihua 2011

机译：用镁和锌试剂合成功能化杂环。非对映选择性加成烯丙基铝试剂加成羰基化合物。芳香族和苄基锰试剂的制备及应用

Diastereoselectivity in the Addition of Allylzinc Reagents to delta-Alkoxy-gamma, delta-disubstituted Alkenyllithium Compounds

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