Chiral 1,2-amino alcohols and 1,2-diamines derived from cyclohexene oxide: Recent applications in asymmetric synthesis
Chiral 1,2-amino alcohols and 1,2-diamines derived from cyclohexene oxide: Recent applications in asymmetric synthesis
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DOI：
10.1055/s-2006-950259
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发表时间：
2006-10-17
期刊：
影响因子：
2
通讯作者：
Juaristi, Eusebio
中科院分区：
文献类型：
--
作者：
de Parrodi, Cecilia Anaya;Juaristi, Eusebio
本文介绍了几种对映体纯的β-氨基醇和β-二胺的简便制备方法，它们已被证明是烯醇化物的烷基化和羰基化合物的氢化等立体选择性反应中的有效配体。此外，标题化合物是各种手性恶唑烷酮、恶嗪酮、膦酰胺等的有用前体，其允许对映选择性地形成多种手性衍生物，包括醇、羟醛缩合产物、氨基膦酸、亚砜等，以及开发用于测定手性醇和手性胺中对映体纯度的衍生试剂。1引言2衍生自氧化环己烯的手性环状1，2-氨基醇2.1对映体纯环状1，由环氧环己烷衍生的2-氨基醇2.2在手性环状1，2-氨基醇作为配体存在下二乙基锌对醛的对映选择性加成2.3手性1，4-恶嗪-2-酮及其非对映选择性α-烷基化反应的研究3顺式和反式六氢苯并恶唑烷-2-酮的合成3.1非对映选择性α-烷基化反应3.2非对映选择性Aldol反应3.3区域选择性和非对映选择性C-酰化3.4立体特异性手性亚磺酰基转移剂3.5立体选择性迈克尔加成3.6非立体选择性叠氮化4衍生自环氧环己烷的手性环状1，2-二胺4.1对映体纯环状1，2-二胺4.2对映纯1，2-二胺的磷酸化衍生物作为手性衍生剂的应用4.3对映纯1，2-二胺存在下苯乙酮的对映选择性还原4.4磺酰胺配体的合成及其在对映选择性烷基化反应中的应用酮的乙烯基化和烯丙基化4.5磷酸化衍生物对醛的非对映选择性加成。
This Account describes convenient procedures for the preparation of several enantiopure beta-amino alcohols and beta-diamines, which have proved to be efficient ligands in relevant stereoselective reactions such as alkylation of enolates and hydrogenation of carbonyl compounds. Furthermore, the title compounds are useful precursors of various chiral oxazolidinones, oxazinones, phosphonamides, etc., which allow the enantioselective formation of a wide variety of chiral derivatives, including alcohols, aldol condensation products, aminophosphonic acids, sulfoxides, and others, as well as the development of derivatizing reagents for the determination of enantiomeric purity in chiral alcohols and chiral amines.1 Introduction2 Chiral Cyclic1,2-Amino Alcohols Derived from Cyclohexene Oxide2.1 Synthesis of Enantiopure Cyclic 1,2-Amino Alcohols Derived from Cyclohexene Oxide2.2 Enantioselective Addition of Diethylzinc to Aldehydes in the Presence of Chiral Cyclic 1,2-Amino Alcohols as Ligands2.3 Synthesis of Chiral 1,4-Oxazin-2-ones and their Diastereo-selective alpha-Alkylation3 Synthesis of cis- and trans-Hexahydrobenzoxazolidin-2-ones and their Application as Chiral Auxiliaries in Asymmetric Synthesis3.1 Diastereoselective alpha-Alkylation3.2 Diastereoselective Aldol Reaction3.3 Regio- and Diastereoselective C-Acylation3.4 Stereospecific Chiral Sulfinyl Transfer Agents3.5 Stereoselective Michael Addition3.6 Diastereoselective Azidation4 Chiral Cyclic 1,2-Diamines Derived from Cyclohexene Oxide4.1 Synthesis of Enantiopure Cyclic 1,2-Diamines4.2 Application of Phosphorylated Derivatives of Enantiopure 1,2-Diamines as Chiral Derivatizing Agents4.3 Enantioselective Reduction of Acetophenone in the Presence of Enantiopure 1,2-Diamines4.4 Synthesis of Sulfonamide Ligands and their Application in the Enantioselective Alkylation, Vinylation and Allylation of Ketones4.5 Diastereoselective Addition of Phosphorylated Derivatives to Aldehydes.