通过N-酰基吡啶鎓及相关盐的还原二聚反应实现C2对称邻二胺的不对称合成。
Asymmetric synthesis of C2-symmetric vicinal diamines via reductive dimerization of N-acylpyridinium and related salts.
作者信息
Bharathi Pandi, Comins Daniel L
机构信息
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
出版信息
Org Lett. 2008 Jan 17;10(2):221-3. doi: 10.1021/ol702595d. Epub 2007 Dec 20.
PMID:18092789
Abstract
A new route to C2-symmetric diamines via an asymmetric reductive dimerization of 1-acylpyridinium salts and their benzo derivatives is described. This method is practical as the starting heterocycles and chiral auxiliaries are readily available. The titanium reducing agent is inexpensive and easy to prepare. Several novel enantiopure C2-symmetric diamine derivatives were synthesized using this method.
摘要
描述了一种通过1-酰基吡啶鎓盐及其苯并衍生物的不对称还原二聚反应制备C2对称二胺的新方法。该方法具有实用性，因为起始杂环和手性助剂易于获得。钛还原剂价格低廉且易于制备。使用该方法合成了几种新型对映体纯的C2对称二胺衍生物。
相似文献
1
Asymmetric synthesis of C2-symmetric vicinal diamines via reductive dimerization of N-acylpyridinium and related salts.通过N-酰基吡啶鎓及相关盐的还原二聚反应实现C2对称邻二胺的不对称合成。
Org Lett. 2008 Jan 17;10(2):221-3. doi: 10.1021/ol702595d. Epub 2007 Dec 20.
2
An advance on exploring N-tert-butanesulfinyl imines in asymmetric synthesis of chiral amines.N-叔丁基亚磺酰亚胺在手性胺不对称合成中的研究进展。
Acc Chem Res. 2008 Jul;41(7):831-40. doi: 10.1021/ar7002623. Epub 2008 Jun 6.
3
Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral pi-allyl Pd-catalyst.通过使用手性π-烯丙基钯催化剂进行对映选择性N-烯丙基化反应催化不对称合成邻二胺衍生物。
Org Lett. 2004 Sep 30;6(20):3605-7. doi: 10.1021/ol048498n.
4
Controlling stereochemical outcomes of asymmetric processes by catalyst remote molecular functionalizations: chiral diamino-oligothiophenes (DATs) as ligands in asymmetric catalysis.通过催化剂远程分子官能化控制不对称过程的立体化学结果：手性二氨基低聚噻吩（DATs）作为不对称催化中的配体。
Chemistry. 2006 Jan 11;12(3):667-75. doi: 10.1002/chem.200500889.
5
Stereocontrolled synthesis of vicinal diamines by organocatalytic asymmetric Mannich reaction of N-protected aminoacetaldehydes: formal synthesis of (-)-agelastatin A.通过 N-保护的氨基乙醛的有机催化不对称 Mannich 反应立体控制合成偕二胺：(-)-agelastatin A 的形式合成。
J Am Chem Soc. 2012 May 2;134(17):7516-20. doi: 10.1021/ja301120z. Epub 2012 Apr 19.
6
Efficient synthesis of a peculiar vicinal diamine semiochemical from Streptomyces natalensis.从链霉菌属纳塔尔变种中高效合成一种特殊的顺式二胺信息素。
Org Lett. 2010 Aug 6;12(15):3522-4. doi: 10.1021/ol1013763.
7
C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine--an intermediate for APN inhibitor.C2-对称的可回收有机催化剂用于对映选择性Strecker 反应合成α-氨基酸和手性二胺-APN 抑制剂的中间体。
J Org Chem. 2012 May 4;77(9):4375-84. doi: 10.1021/jo300349f. Epub 2012 Apr 22.
8
Evaluation of (+)-sparteine-like diamines for asymmetric synthesis.用于不对称合成的（+）-鹰爪豆碱类二胺的评估
J Org Chem. 2004 Aug 20;69(17):5789-92. doi: 10.1021/jo049182w.
9
Ring-opening and -expansion of 2,2'-biaziridine: access to diverse enantiopure linear and bicyclic vicinal diamines.2,2'-双氮杂环丙烷的开环与扩环反应：合成多种对映体纯的直链和双环邻二胺
Org Lett. 2014 Aug 15;16(16):4344-7. doi: 10.1021/ol502164b. Epub 2014 Aug 7.
10
Catalytic enantioselective addition of dialkylzinc reagents to N-acylpyridinium salts.二烷基锌试剂对N-酰基吡啶鎓盐的催化对映选择性加成反应。
Angew Chem Int Ed Engl. 2009;48(49):9339-41. doi: 10.1002/anie.200904981.
Zotero 插件