Hydrogen bonding-based molecular recognition by urea, thiourea and guanidine

被引：3

作者：

Nakanishi, Waka

机构：

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2006年 / 64卷 / 10期

关键词：

thiourea; guanidine; hydrogen bonding; double hydrogen bonding; double activation; metal-free; molecular recognition;

D O I：

10.5059/yukigoseikyokaishi.64.1073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vast number of valuable metal catalyzed reactions has been developed to date. One of the important roles of the metals is the activation of an electrophile as a Lewis acid. On the other hand, due to environmental and economical demands, metal-free reactions have been attracting much attention. In this review, reactions catalyzed by urea, thiourea and guanidine are introduced. These catalysts have more than two active hydrogens, which can activate an electrophile through double hydrogen bonding. High enantio selectivity is achieved by tuning of their side chains.

引用

页码：1073 / 1074

页数：2

共 14 条

[1] Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst
Corey, EJ
Grogan, MJ
[J]. ORGANIC LETTERS, 1999, 1 (01) : 157 - 160
[2] ALTERING THE STEREOCHEMISTRY OF ALLYLATION REACTIONS OF CYCLIC ALPHA-SULFINYL RADICALS WITH DIARYLUREAS
CURRAN, DP
KUO, LH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) : 3259 - 3261
[3] RETRACTED: Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide (Retracted article. See JUN, 2023)
Iyer, MS
Gigstad, KM
Namdev, ND
Lipton, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) : 4910 - 4911
[4] Thiourea-catalyzed enantioselective hydrophosphonylation of imines:: Practical access to enantiomerically enriched α-amino phosphonic acids
Joly, GD
Jacobsen, EN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4102 - 4103
[5] Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea
Okino, T
Hoashi, Y
Furukawa, T
Xu, XN
Takemoto, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) : 119 - 125
[6] Metal-free catalysts for the hydrolysis of RNA derived from guanidines, 2-aminopyridines, and 2-aminobenzimidazoles
Scheffer, U
Strick, A
Ludwig, V
Peter, S
Kalden, E
Göbel, MW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) : 2211 - 2217
[7] Metal-free organocatalysis through explicit hydrogen bonding interactions
Schreiner, PR
[J]. CHEMICAL SOCIETY REVIEWS, 2003, 32 (05) : 289 - 296
[8] Sigman MS, 2000, ANGEW CHEM INT EDIT, V39, P1279, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1279::AID-ANIE1279>3.0.CO
[9] 2-U
[10] Diastereoselective Henry reaction catalyzed by guanidine-thiourea bifunctional organocatalyst
Sohtome, Y
Takemura, N
Iguchi, T
Hashimoto, Y
Nagasawa, K
[J]. SYNLETT, 2006, (01) : 144 - 146

← 1 2 →