6624-05-1Relevant articles and documents
Catalytic asymmetric [4+2]-cycloaddition of dienes with aldehydes
Liu, Luping,Kim, Hyejin,Xie, Youwei,Fares, Christophe,Kaib, Philip S.J.,Goddard, Richard,List, Benjamin
supporting information, p. 13656 - 13659 (2017/11/06)
Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Br?nsted acid catalysts of the hetero-Diels-Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.
A convenient approach for the synthesis of 1,3,5-trioxanes under solvent-free conditions at room temperature
Li, Xinzhong,Lin, Qi,Cao, Rong
, p. 1017 - 1022 (2014/06/09)
A series of environmentally benign bis-SO3H-functionalized Bronsted acidic ionic liquids were synthesized by using aliphatic polyamines and 1,3-propanesultone as the source chemicals. These ionic liquids acted as efficient inexpensive and recyclable catalysts for cyclotrimerization of aliphatic aldehydes at room temperature under solvent-free conditions. The reactions proceeded smoothly with good to excellent isolated yields (66.9-97.6 %=) and were generally complete in 1.5 h when the amount of ionic liquids was 0.1 mol%. The ionic liquids could be recovered readily and reused five times without any significant loss in their catalytic activity. Graphical abstract: [Figure not available: see fulltext.]
Cyclotrimerization of Aliphatic Aldehydes Catalysed by Keggin-type Heteropoly Acids and Concomitant Phase Separation
Sato, Satoshi,Furuta, Hiromi,Sodesawa, Toshiaki,Nozaki, Fumio
, p. 385 - 390 (2007/10/02)
The acid-catalysed cyclotrimerization of aliphatic aldehydes has been examined through comparison of heteropoly acids with other acid catalysts.A Keggin-type heteropoly acid such as phosphomolybdic acid catalyses the cyclotrimerization of aldehydes, such as ethanal, propanal, butanal, 2-methylpropanal, 2,2-dimethylpropanal, hexanal, octanal, and decanal, to produce the respective 2,4,6-trialkyl-1,3,5-trioxanes in high yields.Catalysts turnover number of the heteropoly acid is more than 10000 for propanal cyclotrimerization.In addition to the high catalytic activities, the reaction mixture spontaneously separates into two phases, a produ ct phase and a catalyst phase, at high conversions of aldehyde.For propanal cycltrimerization, the reaction mixture separates into two liquid phases, and the recovered catalyst phase may be repeatedly applied to the reaction without additional care in isolation of the catalyst.The phase separation phenomenon has been concluded to be caused by the insolubility of the heteropoly acid coordinated with propanal in the product 2,4,6-triethyl-1,3,5-trioxane.