One-Pot Synthesis of N-Substituted beta-Amino Alcohols from Aldehydes and Isocyanides

Cioc Razvan C.; van der Niet Daan J. H.; Janssen Elwin; Ruijter Eelco; Orru Romano V. A.

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One-Pot Synthesis of N-Substituted beta-Amino Alcohols from Aldehydes and Isocyanides

机译：由醛和异氰酸酯一锅法合成N取代的β-氨基醇

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A practical two-stage one-pot synthesis of N-substituted -amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, -halo ketones, -halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible.

机译：已经开发出一种实用的两步一锅法合成的N-取代的氨基醇，其使用醛和异氰酸酯作为起始原料。该方法的特点是反应条件温和，范围广，对官能团的耐受性强。基于不太常见的中心碳-碳键断开连接，该协议对涉及胺和各种碳亲电试剂（环氧化物，-卤代酮，-卤代醇）的传统方法进行了补充。如有关抗哮喘药沙丁胺醇的合成所示，可以从简单的结构单元中以简洁有效的方式制备药用相关产品。将合成物升级为对映选择性变体也是可行的。

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《Chemistry: A European journal》 |2015年第21期|共6页
作者
Cioc Razvan C.; van der Niet Daan J. H.; Janssen Elwin; Ruijter Eelco; Orru Romano V. A.;
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正文语种 eng
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aldehydes; amino alcohols; isocyanide; Lewis bases; salbutamol;

机译：醛;氨基醇;异氰酸酯;路易斯碱;沙丁胺醇;

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专利

1. One-Pot Synthesis of N-Substituted beta-Amino Alcohols from Aldehydes and Isocyanides [J] . Cioc Razvan C., van der Niet Daan J. H., Janssen Elwin, Chemistry: A European journal . 2015,第21期

机译：由醛和异氰酸酯一锅法合成N取代的β-氨基醇
2. BORANES IN SYNTHESIS .5. THE HYDROBORATION OF ENAMINES WITH MONO- AND DIALKYLBORANES - ASYMMETRIC SYNTHESIS OF BETA-AMINO ALCOHOLS OF MODERATE ENANTIOMERIC PURITY FROM ALDEHYDE ENAMINES [J] . Fisher GB., Nicholson LW., Hasha DL., The Journal of Organic Chemistry . 1995,第7期

机译：合成中的硼烷.5。氨基与二烷基硼烷加氢加氢硼酸酯-醛类中间体中度对映体纯的β-氨基醇的不对称合成
3. One-Pot Conversion of alpha-Amino Acids into beta-Amino Aldehydes or 2-Acetoxyazetidines: Application to the Synthesis of Modified Peptides [J] . Boto A, Hernandez R, Saavedra CJ Synlett . 2010,第4期

机译：一锅法将α-氨基酸转化为β-氨基乙醛或2-乙酰氧基氮杂环丁烷：在修饰肽合成中的应用
4. ENANTIOCOMPLEMENTARY SYNTHESIS OF CHIRAL ALCOHOLS COMBINING PHOTOCATALYSIS AND WHOLE-CELL BIOCATALYSIS IN A ONE-POT CASCADE PROCESS [C] . Yongzhen Peng, Jian Xu, Xianfu Lin, Conference on biochemical and molecular engineering . 2019

机译：一锅级联过程中光催化与全细胞生物催化相结合的手性醇的对映体合成
5. Part I. One-pot synthesis of secondary alcohols and one-pot asymmetric synthesis of secondary propargylic alcohols. Part II. Redox isomerization of secondary propargylic alcohols to enones. Part III. Synthesis study towards C9-C14 fragment of (+)-discodermolide. Part IV. Asymmetric synthesis of anti, anti-stereotriad building blocks for polypropionate natural products [D] . Xie, Qiuzhe 2007

机译：第一部分：仲醇的一锅法合成和仲炔丙醇的一锅法不对称合成。第二部分仲炔丙醇的氧化还原异构化为烯酮。第三部分（+）-discodermolide C9-C14片段的合成研究。第四部分聚丙烯酸酯天然产物的抗，抗立体三环构建基的不对称合成
6. One-pot synthesis of epoxides from benzyl alcohols and aldehydes [O] . Edwin Alfonzo, Jesse W L Mendoza, Aaron B Beeler 2018

机译：一锅法从苄醇和醛合成环氧化物
7. One-pot synthesis of amides by aerobic oxidative coupling of alcohols or aldehydes with amines using supported gold and base as catalysts [O] . Kegnæs Søren, Mielby Jerrik Jørgen, Mentzel Uffe Vie, 2012

机译：使用负载的金和碱作为催化剂，通过醇或醛与胺的有氧氧化偶联一锅法合成酰胺
8. Use of Nitrone Cycloadditions in the Synthesis of Beta-Amino Aldehydes and Unsaturated Amines [R] . Lander, S. W. 1986

机译：硝酮环加成反应在β-氨基醛和不饱和胺合成中的应用

One-Pot Synthesis of N-Substituted beta-Amino Alcohols from Aldehydes and Isocyanides

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