415920-00-2Relevant academic research and scientific papers
Highly Enantioselective Ring-Opening of meso-Epoxides with O- and N-Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex
Malatinec, ?tefan,Bedná?ová, Eva,Tanaka, Hiroki,Kotora, Martin
supporting information, p. 1249 - 1257 (2021/02/03)
The ring-opening of epoxides is a synthetically significant process widely applied in all kinds of chemistry. Herein, we report the catalytic and highly enantioselective variant of this reaction exploiting our recent endeavors to design and synthesize chi
Scandium-bipyridine-catalyzed, enantioselective alcoholysis of meso-epoxides
Tschoep, Andreas,Marx, Andreas,Sreekanth, Anakallil R.,Schneider, Christoph
, p. 2318 - 2327 (2008/02/08)
The scandium-bipyridine-catalyzed ring-opening of meso-epoxides with aliphatic alcohols has been studied. Aromatic epoxides were ring-opened with >90 % ee furnishing valuable 1,2-diol monoethers in typically good yields whereas aliphatic epoxides gave ris
Scandium-bipyridine-catalyzed enantioselective addition of alcohols and amines to meso-epoxides
Schneider, Christoph,Sreekanth, Anakallil R.,Mai, Enzo
, p. 5691 - 5694 (2007/10/03)
A winning combination of metal and ligand: The catalyst formed in situ from Sc(OTf)3 and bipyridine 1 (10 mol%) mediates the alcoholysis and aminolysis of Mieso-epoxides in high enantioselectivities and furnishes valuable chiral 1,2-diol monoethers 2 and 1,2-amino alcohols 3 as products (PMB = para-methoxybenzyl).
Catalytic asymmetric aldol reactions in aqueous media using chiral bis-pyridino-18-crown-6 - Rare earth metal triflate complexes
Hamada, Tomoaki,Manabe, Kei,Ishikawa, Shunpei,Nagayama, Satoshi,Shiro, Motoo,Kobayashi, Sho
, p. 2989 - 2996 (2007/10/03)
Catalytic asymmetric aldol reactions in aqueous media have been developed using Pr(OTf)3 and chiral bis-pyrdino-18-crown-6 1. In the asymmetric aldol reaction using rare earth metal triflates (RE(OTf)3) and 1, slight changes in the i
Monobenzylethers of (R,R)-1,2-diphenylethane-1,2-diol as a possible alternative to cyclohexyl-based chiral auxiliaries in the stereoselective reduction of α-ketoesters
Scafato, Patrizia,Leo, Laura,Superchi, Stefano,Rosini, Carlo
, p. 153 - 159 (2007/10/03)
The monobenzylethers of (R,R)-1,2-diphenylethane-1,2-diol have been used as chiral auxiliaries in the stereoselective reduction of the corresponding phenylglyoxylates. The diastereoselectivity of the reduction with either L-selectride or DIBAL was found to be strictly dependent on the nature of the substitution on the aromatic ring of the auxiliary and a maximum d.r. of 87:13 was obtained with the p-CF3 substituted derivative. This investigation also shows that with open chain chiral auxiliaries diastereoselectivities of preparative interest can be achieved, suggesting that such auxiliaries can constitute a promising alternative to the commonest cyclohexyl-based ones.
