Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst

2014 ◽  
Vol 12 (10) ◽  
pp. 1547-1550 ◽  
Author(s):  
Ming Yu Jin ◽  
Sun Min Kim ◽  
Hui Mao ◽  
Do Hyun Ryu ◽  
Choong Eui Song ◽  
...  
Keyword(s):  
Aromatic Aldehyde ◽  
Aliphatic Aldehyde ◽  
Aliphatic Aldehydes ◽  
Condensation Reactions

Chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio.

Enantioselective Preparation of Alcohols and Amines:The Suh Synthesis of (-)-Macrosphelide J

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
Aliphatic Aldehyde ◽  
Geometric Control ◽  
Cinchona Alkaloid ◽  
University Of Virginia ◽  
Aliphatic Aldehydes ◽  
Salen Complex ◽  
Complementary Approach ◽  
National University ◽  
The University

Keiji Maruoka of Kyoto University (J. Am. Chem. Soc. 2009, 131, 3450) and Yujiro Hayashi of the Tokyo University of Science (Chem. Commun. 2009, 3083) independently developed organocatalysts for the enantioselective α-benzoylation of aliphatic aldehydes such as 1. The product 3 can be readily carried on to, inter alia, either enantiomer of the epoxide. Chengjian Zhu of Nanjing University designed (Adv. Synth. Cat. 2009, 351, 920) a chiral salen complex that mediated the enantioselective opening of both cyclohexene oxide (4) and cyclopentene oxide. This reagent combination might also engage just one of the two enantiomers of a racemic cycloalkene epoxide. Lin Pu of the University of Virginia established (Organic Lett. 2009, 11, 2441) a BINOL catalyst for the addition of ethyl propiolate 7 to an aliphatic aldehyde 6 to give the alcohol 8 in high ee. In a complementary approach, Do Hyun Ryu of Sungkyunkwan University found (Angew. Chem. Int. Ed. 2009, 48, 4398) that an oxazaborolidinium salt catalyzed the addition of 7 to 9 to give 10 with high ee and high geometric control. Jianliang Xiao of the University of Liverpool devised (J. Am. Chem. Soc. 2009, 131, 6967) an Ir catalyst for the enantioselective reductive amination of a ketone 11 to the amine 13 . Karl B. Hansen, Yi Hsiao. and Feng Xu, then all at Merck/Rahway, showed (J. Am. Chem. Soc. 2009, 131, 8798) that it was possible to hydrogenate a vinylogous primary amide 14 to the amine 15 with high enantiocontrol. Takashi Ooi of Nagoya University designed (J. Am. Chem. Soc. 2009, 131, 7242) a chiral P-spiro tetraaminophosphonium catalyst that mediated the enantioselective addition of anilines to nitroalkenes such as 16. The product 18 could be carried on to the 1,2-diamine, or to the α-amino acid. Masahiro Terada of Tohoku University devised (Angew. Chem. Int. Ed. 2009, 48, 2553) a BINOL-derived phosphonic acid to catalyze the enantioselective 1,2-addition of the enamide 20 to the imine derived from 19. Yixin Lu of the National University of Singapore found (Organic Lett. 2009, 11, 1721) that a cinchona alkaloid-derived thiourea effectively catalyzed the enantioselective conjugate addition of nitroalkanes such as 22 to the acceptor 23.

Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

2018 ◽  
Vol 54 (4) ◽  
pp. 374-377 ◽  
Author(s):  
Takahiro Kawajiri ◽  
Reiya Ohta ◽  
Hiromichi Fujioka ◽  
Hironao Sajiki ◽  
Yoshinari Sawama
Keyword(s):  
Aromatic Aldehyde ◽  
Aldol Reaction ◽  
Aliphatic Aldehydes ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Aldol Addition

Unprecedented chemoselectivity between aromatic and aliphatic aldehydes has been achieved in the Mukaiyama aldol reaction using aldehyde-derived silyl enol ethers.

Highly Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by Chiral Phosphoric Acids

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2041-2045 ◽  
Author(s):  
Yongbiao Guo ◽  
Chuanpin Zou ◽  
Zhenhua Gao ◽  
Xiangyan Meng ◽  
Guilan Huang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Biginelli Reaction ◽  
Aliphatic Aldehyde ◽  
Reaction Conditions ◽  
Aliphatic Aldehydes ◽  
Keto Ester ◽  
Chiral Phosphoric Acid ◽  
Three Component Reaction ◽  
High Yields ◽  
Phosphoric Acids

Several chiral phosphoric acids were evaluated as organocatalysts for the enantioselective Biginelli reaction of aliphatic aldehydes. With a chiral phosphoric acid derived from 3,3′-bis(3,5-di-tert-butyl-4-methoxyphenyl)-1,1′-binaphthalene-2,2′-diol, and after extensive optimization of the reaction conditions, the corresponding dihydropyrimidines were obtained in moderate to high yields with 73–87% ee by a three-component reaction of an aliphatic aldehyde, urea, and a β-keto ester.

scholarly journals Biginelli condensation of aliphatic aldehydes catalysed by zinc methanesulfonate

2005 ◽  
Vol 2005 (11) ◽  
pp. 691-693 ◽  
Author(s):  
Min Wang ◽  
Heng Jiang ◽  
Zhichang Wang
Keyword(s):  
Aliphatic Aldehyde ◽  
Absolute Ethanol ◽  
Aliphatic Aldehydes ◽  
Dicarbonyl Compound ◽  
Wide Range ◽  
Biginelli Condensation

Three-component condensation of an aliphatic aldehyde, 1,3-dicarbonyl compound and urea proceeds efficiently in absolute ethanol under refluxing temperature using zinc methanesulfonate as a catalyst to afford corresponding 3,4-dihydropyrimidinone. The catalyst can be reused for several times without distinct decrease in reaction yields. The procedure is very useful for the synthesis of dihydropyrimidinones with a wide range of aliphatic aldehydes.

Visible-light mediated directed perfluoroalkylation of hydrazones

2017 ◽  
Vol 15 (28) ◽  
pp. 6014-6023 ◽  
Author(s):  
Heng Ji ◽  
Hui-qiong Ni ◽  
Peng Zhi ◽  
Zi-wei Xi ◽  
Wei Wang ◽  
...  
Keyword(s):  
Visible Light ◽  
Aromatic Aldehyde ◽  
Aliphatic Aldehyde

A convenient and efficient protocol was reported to access a series of perfluoroalkylated aromatic aldehyde hydrazones. Aliphatic aldehyde hydrazones and N-monosubstituted hydrazones which are unreactive in previously reported hydrazone perfluoroalkylation reactions now take part in the reaction.

The reaction of O-benzoyl aromatic aldehyde cyanohydrin with aliphatic aldehyde

1975 ◽  
Vol 16 (11) ◽  
pp. 903-906 ◽  
Author(s):  
Masatomo Hamana ◽  
Toshiyasu Endo ◽  
Seitaro Saeki
Keyword(s):  
Aromatic Aldehyde ◽  
Aliphatic Aldehyde
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