Aminative Umpolung Synthesis of Aryl Vicinal Diamines from Aromatic Aldehydes

被引：45
作者：
Liu, Xuliang [1 ,2 ]
Gao, Ang [1 ,2 ]
Ding, Lei [1 ,2 ]
Xu, Juan [1 ,2 ]
Zhao, Baoguo [1 ,2 ,3 ]
机构：
[1] Shanghai Normal Univ, Key Lab Resource Chem, Educ Minist, Shanghai 200234, Peoples R China
[2] Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Shanghai 200234, Peoples R China
[3] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 08期
关键词：
ASYMMETRIC ALLYLIC ALKYLATION; CATALYZED DECARBOXYLATIVE ALLYLATION; TERT-BUTANESULFINYL IMINES; BETA-AMINO ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; THIOAMIDE DIANIONS; COUPLING REACTIONS; 2-AMINO ALCOHOLS; MANNICH REACTION;
D O I：
10.1021/ol500522d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this paper an aminative umpolung synthesis of aryl vicinal diamines from aldehydes and N-Ts imines is described. Electrophilic aromatic aldehydes were smoothly converted into delocalized 2-azaallylanions via condensation with 2,2-diphenylglycine in methanol and subsequent decarboxylation in THF and underwent further reaction with N-Ts imines to give a variety of 1,2-diamine derivatives in good yields with high syn/anti diastereoselectivity.
引用
收藏
页码：2118 / 2121
页数：4
相关论文
共 89 条
[1]  
Ahlbrecht H., 1994, SYNTHESIS, P719
[2]  
Albert J., 2007, PCT Int. Appl., Patent No. [WO 2007058601 A1 20070524, 2007058601]
[3]   Synthesis of enantiomerically pure C2-symmetric acyclic and cyclic 1,2-diamines via pinacol coupling of imines [J].
Annunziata, R ;
Benaglia, M ;
Caporale, M ;
Raimondi, L .
TETRAHEDRON-ASYMMETRY, 2002, 13 (24) :2727-2734
[4]  
[Anonymous], 2007, EUR J ORG CHEM
[5]   Synthesis of 2,3-disubstituted pyrrolidines by intramolecular addition of α-aminoalkyl radicals to electron deficient C=C bonds [J].
Aurrecoechea, JM ;
Fernández, A ;
Gorgojo, JM ;
Saornil, C .
TETRAHEDRON, 1999, 55 (23) :7345-7362
[6]   Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].
Beak, P ;
Basu, A ;
Gallagher, DJ ;
Park, YS ;
Thayumanavan, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560
[7]   The enantioselective Tsuji allylation [J].
Behenna, DC ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045
[8]  
Behenna DC, 2012, NAT CHEM, V4, P130, DOI [10.1038/nchem.1222, 10.1038/NCHEM.1222]
[9]   Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].
Bugaut, Xavier ;
Glorius, Frank .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522
[10]   Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate [J].
Burger, EC ;
Tunge, JA .
ORGANIC LETTERS, 2004, 6 (22) :4113-4115
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