Organocatalysed Asymmetric beta-Animation and Multicomponent syn-Selective Diamination of alpha,beta-Unsaturated Aldehydes

Hao Jiang; Johanne B.Nielsen; Martin Nielsen

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Organocatalysed Asymmetric beta-Animation and Multicomponent syn-Selective Diamination of alpha,beta-Unsaturated Aldehydes

机译：有机催化的α-β-不饱和醛类的不对称β-动画和多组分同选择氨基化

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摘要

An easy and affordable route for obtaining chiral beta-aminated-and alpha,beta-diaminated aldehydes,1,3-aminoal-cohols,and related compounds by using organocatalysis is presented.The chiral secondary amine(S)-2-[bis(3,5-bistrifluoromethylphenyl)trimethylsila-nyloxymethyl]pyrrolidine is used as the catalyst to activate alpha,beta-unsaturated aldehydes,which allows succinimide to add in a 1,4-regio-and stereoselective fashion thereby forming N-protected 1,3-aminoaldehydes in good yields and enantioselectivities.This is followed by two easy transformations giving rise to optically active 1,3-aminoalcohols,a common motif in many biologically active compounds,for example,fibrinogen receptor antagonists.Furthermore,optically active alpha,beta-syn-diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one-pot reaction.

机译：提出了一种通过有机催化获得手性β-氨基和α，β-二氨基乙醛，1,3-氨基醇及相关化合物的简便且经济的途径。手性仲胺（S）-2- [bis（ 3,5-双三氟甲基苯基）三甲基硅烷基-甲氧基甲基]吡咯烷用作活化α，β-不饱和醛的催化剂，它可使琥珀酰亚胺以1,4-区域和立体选择性方式加入，从而形成受N保护的1,3-氨基醛具有良好的收率和对映选择性。随后进行了两次简单的转化，产生了光学活性的1,3-氨基醇，这是许多生物活性化合物（例如纤维蛋白原受体拮抗剂）中的常见基序。此外，光学活性的α，β-syn通过一锅反应中添加偶氮二羧酸二乙酯获得二价乙醛。

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《Chemistry: A European journal》 |2007年第32期|共8页
作者
Hao Jiang; Johanne B.Nielsen; Martin Nielsen;
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正文语种 eng
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animation; asymmetry; multicomponent diamination organocatalysis;

机译：动画;不对称;多组分渗碳有机催化;

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专利

1. Organocatalysed Asymmetric beta-Animation and Multicomponent syn-Selective Diamination of alpha,beta-Unsaturated Aldehydes [J] . Hao Jiang, Johanne B.Nielsen, Martin Nielsen Chemistry: A European journal . 2007,第32期

机译：有机催化的α-β-不饱和醛类的不对称β-动画和多组分同选择氨基化
2. One-step synthesis of thiazolo[3,2-alpha]pyridines by a multicomponent reaction of beta-enaminonitriles, alpha,beta-unsaturated aldehydes, and 2-aminothiol hydrochlorides [J] . Perrino MP, del Villar-Guerra R, Sanudo MC, Tetrahedron . 2010,第15期

机译：通过β-烯腈，α，β-不饱和醛和2-氨基硫醇盐酸盐的多组分反应一步合成噻唑并[3,2-α]吡啶
3. Organocatalytic and direct asymmetric vinylogous Michael addition of alpha,alpha-dicyanoolefins to alpha,beta-unsaturated aldehydes [J] . Xie JW, Yue L, Xue D, Chemical Communications . 2006,第14期

机译：α，α-二氰基烯烃向α，β-不饱和醛的有机催化和直接不对称乙烯基迈克尔加成
4. Mass Spectrometric Characterization of Covalent Modification of Human Serum Albumin by alpha,beta-Unsaturated Aldehydes [C] . Qingyuan Liu, Scott Gronert ASMS Conference on Mass Spectrometry and Allied Topics . 2008

机译：α，β-不饱和醛类人血清白蛋白的共价修饰的质谱表征
5. I. Studies Towards the Total Synthesis of (+)-Iriomoteolide-1a II. Asymmetric S(E)' Reactions of E/Z-alpha,beta-Unsaturated Aldehydes. [D] . Atwater, Bruce Aubrey. 2013

机译：I.关于（+）-碘代内酰胺-1a的全合成的研究II。 E /Z-α，β-不饱和醛的不对称S（E）'反应。
6. Cu(I)-Catalyzed Diamination of Conjugated Olefins with Tunable Anionic Counterions. A Possible Approach to Asymmetric Diamination [O] . Baoguo Zhao, Haifeng Du, Yian Shi -1

机译：铜（I）催化与可调阴离子抗衡共轭烯烃Diamination的。一种可能的方法以非对称Diamination
7. Stereoretentive Addition of N-tert-Butylsulfonyl-alpha-Amido Silanes to Aldehydes, Ketones, alpha,beta-Unsaturated Esters, and Imines [O] . Mita, Tsuyoshi, Saito, Keisuke, Sugawara, Masumi, 2016

机译：N-叔丁基磺酰基-α-氨基硅烷与醛，酮，α，β-不饱和酯和亚胺的立体定向加成
8. 9-Borabicyclo(3.3.1)nonane as a Highly Selective Reducing Agent for the Facile Conversion of alpha, beta-Unsaturated Aldehydes and Ketones to the Corresponding Allylic Alcohols in the Presence of Other Functional Groups. [R] . Krishnamurthy, S., Brown, H. C. 1975

机译：9-Borabicyclo（3.3.1）壬烷作为高选择性还原剂，用于在其他官能团存在下将α，β-不饱和醛和酮轻易转化为相应的烯丙醇。

Organocatalysed Asymmetric beta-Animation and Multicomponent syn-Selective Diamination of alpha,beta-Unsaturated Aldehydes

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