35216-79-6Relevant academic research and scientific papers
Fluxionally chiral DMAP catalysts: Kinetic resolution of axially chiral biaryl compounds
Ma, Gaoyuan,Deng, Jun,Sibi, Mukund P.
supporting information, p. 11818 - 11821 (2015/03/13)
Can organocatalysts that incorporate fluxional groups provide enhanced selectivity in asymmetric transformations? To address this issue, we have designed chiral 4-dimethylaminopyridine (DMAP) catalysts with fluxional chirality. These catalysts were found
Steric effects of nucleophile-radical coupling reaction. Determination of rate constants for the reaction of aryl radicals with 2-naphthoxide anion
Tempesti, Tomas C.,Pierini, Adriana B.,Baumgartner, Maria T.
experimental part, p. 1523 - 1528 (2009/10/30)
The absolute rate constants for the reaction of different aryl radicals with 2-naphthoxide anion were determined using an indirect method, a competition of the coupling reaction with the H-atom abstraction. We here show that the radical-ambident nucleophi
Highly enantioselective benzylic hydroxylation with concave type of (salen)manganese(III) complex
Hamada, Tetsuya,Irie, Ryo,Mihara, Jun,Hamachi, Kiyoe,Katsuki, Tsutomu
, p. 10017 - 10028 (2007/10/03)
Newly-designed optically active (salen)manganese(III) complexes (5) catalyze highly enantioselective benzylic hydroxylation and moderate level of enantiomer-differentiating oxidation (kinetic resolution) of the resulting benzylic alcohols. Thus, the enantiomeric excess of hydroxylation product was increased through kinetic resolution, as the reaction time was prolonged. For example, enantiomeric excess of 3,3-dimethylindan-1-ol, the hydroxylation product of 1,1-dimethylindan using 5a as a catalyst in chlorobenzene, was 84% alter 10 min and 90% after 20 h.
Investigation of the Diastereoselectivity in the Addition of Organometallics to the α-Keto Esters of Axially Chiral 1,1'-Binaphthalen-2-ol Derivatives
Tamai, Yasufumi,Nakano, Tomoyuki,Miyano, Sotaro
, p. 439 - 446 (2007/10/02)
The inherent chiral induction abilities of axially chiral 2'-substituted 1,1'-binaphthalen-2-ols 2a-f as the chiral auxiliary for the addition of organometallics to their α-keto acid esters were examined as a function of the following reaction variables: size of the 2'-substituent, nature of the organometallic reagent, solvent, and temperature.In the addition of MeMgI to the phenylglyoxylates 3a-f of the alcohols 2a-f, the corresponding atrolactic acid esters 5a-f and 6a-f were obtained with up to 52percent diastereoisomeric excess (d.e.).The preferred diastereoisomer depended on the size of the 2'-substituent, and thus could not solely be determined by the helicity of the 1,1'-binaphthalene framework.By using MeZnI as the nucleophile, the selectivity increased up to 84percent d.e. with the same diastereofacial selectivity as that of MeMgI.On the other hand, the diastereofacial selection was reversed when MeTiCl3 was employed as the nucleophile, with low selectivity (14percent d.e.).It is concluded that MeMgI or MeZnI, as a nucleophile of low Lewis acidity, adds to the keto ester moiety in the s-trans conformation, while the strong Lewis acid MeTiCl3 mainly adds to the s-cis conformer from the same direction as that of the Grignard addition, thus giving the opposite diastereoisomer.
PHOTOSTIMULATED REACTION OF ARYL IODIDES WITH 2-NAPHTHOXIDE IONS BY THE SRN1 MECHANISM
Pierini, A. B.,Baumgartner, M. T.,Rossi, R. A.
, p. 3429 - 3432 (2007/10/02)
The photostimulated reactions of p-iodoanisole (2) and 1-iodonaphthalene (7) with 2-naphthoxide ions in liquid ammonia gave the corresponding 1-aryl-2-naphthols as the only substitution product.These reactions are proposed to proceed via the SRN1 mechanism for nucleophilic aromatic substitution.
