113565-51-8Relevant articles and documents
Carbinol derivatives via rhodium-catalyzed addition of potassium trifluoro(organo)borates to aldehydes
Pucheault, Mathieu,Darses, Sylvain,Genet, Jean-Pierre
, p. 4714 - 4716 (2005)
Reaction of potassium aryltrifluoroborates with aldehydes, in the presence of a rhodium catalyst, afforded carbinol derivatives in high yields under mild aqueous conditions; this efficient reaction proved to be general, allowing the production of highly hindered diarylmethanols and aliphatic aldehydes were also reactive under these conditions. The Royal Society of Chemistry 2005.
Rhodium-catalyzed addition of organoboronic acids to aldehydes
Sakai, Masaaki,Ueda, Masato,Miyaura, Norio
, p. 3279 - 3281 (1998)
Highly inert to ionic additions to aldehydes, aryl- and 1- alkenylboronic acids succumb to a catalytic variant mediated by a [Rh(acac)(CO)2]-diphosphane complex in aqueous phase at 80-95°C to yield secondary alcohols [Eq. (a)]. A key step in the catalytic cycle is the transmetalation between the boron reagent and the rhodium complex. L(n) = diphosphane (e.g. 1,1'-bis(diphenylphosphanyl)ferrocene); R = aryl, 1- alkenyl; R'= alkyl, aryl; acac = acetylacetonate.
Newly synthesized furanoside-based NHC ligands for the arylation of aldehydes
Denizalti, Serpil,?etin Telli, Fatma,Yildiran, Selin,Salman, Azize Ye?im,?etinkaya, Bekir
, p. 689 - 697 (2016)
New furanoside-based NHC precursor salts (2) were synthesized using amino alcohols from the chloralose derivatives of glucose (a), galactose (b), and mannose (c). The novel compounds were fully characterized by 1H NMR, 13C NMR, and elemental analyses. The catalytic activities of these salts were tested in the arylation of aldehydes as catalysts that were generated in situ from [RhCl(COD)]2. In addition, 2a was converted to the rhodium complex 3a in order to compare the results obtained in situ. The newly synthesized compounds were very efficient in terms of yield; nevertheless they did not exhibit a chiral induction.
Ultrasound in Organic Synthesis. 12. In Situ Generation and Uses of Buthyllithium Reagents in Several Synthetic Reactions
Einhorn, J.,Luche, J. L.
, p. 4124 - 4126 (1987)
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High-pressure and thermally induced intramolecular Diets-Alder reactions of furfuryl fumarates. Influence of tether substituents on diastereoselectivity
Butz, Thomas,Sauer, Juergen
, p. 703 - 714 (1997)
Asymmetric intramolecular Diels-Alder (IMDA) reactions of optically active furfuryl fumarates result after crystallization in enantiopure 7-oxabicyclo[2.2.1]heptene derivatives that may be useful building blocks for natural product synthesis. The influenc
Synthesis, characterization, and structures of arylaluminum reagents and asymmetric arylation of aldehydes catalyzed by a titanium complex of an N-sulfonylated amino alcohol
Zhou, Shuangliu,Chuang, Da-Wei,Chang, Shih-Ju,Gau, Han-Mou
, p. 1407 - 1412 (2009)
A series of phenylaluminum reagents AlPhxEt3-x(L) (x = 1-3) containing adduct ligand L [Et2O, THF, OPPh3, or 4-dimethylaminopyridine (DMAP)] were synthesized and characterized. NMR studies showed that AlPhx
On the stereoselectivity of the Paternò-Büchi reaction between carbonyl compounds and 2-furylmethanol derivatives. The case of aliphatic aldehydes and ketones
D'Auria, Maurizio,Emanuele, Lucia,Poggi, Gabriella,Racioppi, Rocco,Romaniello, Gianfranco
, p. 5045 - 5051 (2002)
The Paternò-Büchi reaction between 2-furylmethanol derivatives and aliphatic aldehydes and ketones induced by irradiation through Vycor at 8°C shows high regioselectivity but no stereoselectivity. This behaviour can be rationalised by assuming that this type of compound reacts through both singlet and triplet excited states. Ab initio calculations are in agreement with the formation of the 1,4-biradical. The more stable biradical accounts for the observed regioselectivity. The lack of stereoselectivity was discussed on the basis of two hypotheses. The allylic strain proposed by Adam does not account for the observed results. On the contrary, hydrogen bond interaction between (triplet excited) carbonyl oxygen and hydroxy group is able to describe the observed behaviour.
Binaphthyl-prolinol chiral ligands: Design and their application in enantioselective arylation of aromatic aldehydes
Yao, Chao,Chen, Yaoqi,Sun, Ruize,Wang, Chao,Huang, Yue,Li, Lin,Li, Yue-Ming
supporting information, p. 3644 - 3655 (2021/05/04)
Binaphthyl-prolinol ligands were designed and applied in enantioselective arylation of aromatic aldehydes and sequential arylation-lactonization of methyl 2-formylbenzoate. Under optimized conditions, the reactions provided the desired diarylmethanols and 3-aryl phthalides in up to 96% yields with up to 99% ee and up to 89% yields with up to 99% ee, respectively. In particular, essentially optically pure 3-aryl phthalides (over 99% ee) were obtained in large quantities through recrystallization. This journal is
Isomerization of Propargyl Ethers of 2-Hydroxyoxiranes to Furan Derivatives on Silver Catalysts
Talybov, G. M.
, p. 1153 - 1156 (2021/08/06)
Abstract: It was shown that propargyl ethers of 2-hydroxyoxiranes in the presence of asilver salt of a molybdenum heteropoly acid as a catalyst leads to the formationof furan derivatives with a yield of up to 62.3% and highregioselectivity. [Figure not available: see fulltext.]
