立体选择性地合成杂芳亚甲基取代的吡咯烷：完全有机催化的曼尼希氨化反应。
Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich-hydroamination reactions.
机构信息
Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen, CNRS UMR, 6 boulevard du Marechal Juin, 14050 Caen, France.
出版信息
Chem Commun (Camb). 2013 Feb 25;49(16):1651-3. doi: 10.1039/c2cc38954a.
PMID:23340658
Abstract
A one-pot sequence of organocatalytic transformations delivers heteroarylmethylene-substituted pyrrolidines with high stereo- and enantioselectivity. A Mannich coupling of N-heteroarylalkyne aldehydes with aldimine and an original metal-free hydroamination of the resulting adducts are the key transformations of the process delivering highly functionalized molecules with high potential for synthetic applications.
摘要
一锅法的有机催化转化过程可以高立体选择性和对映选择性地得到杂芳亚甲基取代的吡咯烷。该过程的关键转化是 N-杂芳基炔醛与亚胺的曼尼希缩合反应，以及生成的加合物的新型无金属氢胺化反应，这两个反应可以得到具有高合成应用潜力的高度官能化分子。
相似文献
1
Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich-hydroamination reactions.立体选择性地合成杂芳亚甲基取代的吡咯烷：完全有机催化的曼尼希氨化反应。
Chem Commun (Camb). 2013 Feb 25;49(16):1651-3. doi: 10.1039/c2cc38954a.
2
An organocatalytic direct Mannich-cyclization cascade as [3+2] annulation: asymmetric synthesis of 2,3-substituted pyrrolidines.有机催化直接曼尼希环化级联反应作为 [3+2] 环加成：2,3-取代吡咯烷的不对称合成。
Chem Commun (Camb). 2012 Jul 14;48(55):6975-7. doi: 10.1039/c2cc33103a. Epub 2012 Jun 7.
3
Cycloaddition of chiral tert-butanesulfinimines with trimethylenemethane.手性叔丁基亚磺亚胺与三亚甲基甲烷的环加成反应。
Org Lett. 2013 Apr 19;15(8):2030-3. doi: 10.1021/ol400720b. Epub 2013 Apr 4.
4
Highly enantio- and diastereoselective organocatalytic cascade aza-Michael-Michael reactions: a direct method for the synthesis of trisubstituted chiral pyrrolidines.高度对映选择性和非对映选择性有机催化级联氮杂迈克尔-迈克尔反应：一种合成三取代手性吡咯烷的直接方法。
Chem Commun (Camb). 2008 Nov 21(43):5636-8. doi: 10.1039/b812464g. Epub 2008 Sep 30.
5
A new synthesis of pyrrolidines by way of an enantioselective Mannich/diastereoselective hydroamination reaction sequence.通过对映选择性曼尼希/非对映选择性氨化反应序列，合成吡咯烷。
Org Lett. 2011 Aug 5;13(15):4056-9. doi: 10.1021/ol201566u. Epub 2011 Jul 12.
6
Highly efficient asymmetric anti-Mannich reactions of carbonyl compounds with N-carbamoyl imines catalyzed by amino-thiourea organocatalysts.手性氨基硫脲有机催化剂促进的羰基化合物与 N-氨甲酰亚胺的高效不对称反 Mannich 反应。
Org Biomol Chem. 2012 May 14;10(18):3730-8. doi: 10.1039/c2ob00049k. Epub 2012 Mar 26.
7
Highly active organocatalysts for asymmetric anti-Mannich reactions.高活性有机催化剂用于不对称反 Mannich 反应。
Chemistry. 2011 Aug 1;17(32):8780-3. doi: 10.1002/chem.201101513. Epub 2011 Jul 6.
8
Diastereoselective synthesis of pyrrolidine derivatives via a one-pot nitro-Mannich/hydroamination cascade using base and gold catalysis.一锅法通过碱和金催化的硝基-Mannich/氨化串联反应立体选择性合成吡咯烷衍生物。
Chem Commun (Camb). 2013 Apr 7;49(27):2777-9. doi: 10.1039/c3cc40729b.
9
The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles.直接有机催化不对称曼尼希反应：以未修饰的醛作为亲核试剂。
J Org Chem. 2003 Dec 12;68(25):9624-34. doi: 10.1021/jo0347359.
10
Enantioselective construction of highly substituted pyrrolidines by palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with ketimines.钯催化三甲基烯丙基甲烷与亚胺的不对称 [3+2] 环加成反应构建高取代吡咯烷。
J Am Chem Soc. 2010 Jun 23;132(24):8238-40. doi: 10.1021/ja102102d.
引用本文的文献
1
One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis.一锅法不对称硝基-曼尼希/氢胺化串联反应合成吡咯烷衍生物：有机催化与金催化相结合
ACS Catal. 2014 Feb 7;4(2):634-638. doi: 10.1021/cs401008v. Epub 2014 Jan 6.
2
An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles.一种通过有机催化方法构建 2-杂芳基亚甲基修饰的 N-芳基吡咯的途径。
Beilstein J Org Chem. 2013 Jul 24;9:1480-6. doi: 10.3762/bjoc.9.168. eCollection 2013.
Zotero 插件