104662-02-4Relevant articles and documents
Highly Enantioselective Additions of Diethylzinc to Aldehydes Using 2-Triflamido-methyl-2′-hydroxy-1 ,1′-binaphthyl
Kang, Seung-Wan,Ko, Dong-Hyun,Kim, Kyoung Hoon,Ha, Deok-Chan
, p. 4517 - 4519 (2003)
(Equation presented) A new N-triflated amino alcohol-titanium catalyst was designed for the asymmetric ethylation of aldehydes. This binaphthyl-based sulfonamido alcohol ligand shows uniformly high yield and enantioselectivity in the diethylzinc additions
Asymmetric reduction. A convenient method for the reduction of alkynyl ketones
Parker, Kathlyn A.,Ledeboer, Mark W.
, p. 3214 - 3217 (1996)
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Enantioselective dialkylzinc addition to aldehydes catalyzed by chiral Zn(II)-BINOLates bearing phosphonates and phosphoramides in the 3,3′-positions
Hatano, Manabu,Miyamoto, Takashi,Ishihara, Kazuaki
, p. 1762 - 1764 (2006)
Highly enantioselective dialkylzinc addition to a series of aldehydes was developed based on chiral Zn(II)-BINOLate catalysts bearing phosphonates [P(=O)(OR)2] and phosphoramides [P(=O)(NMe2)2] at the 3,3′-positions. The reactions proceeded smoothly and showed reductions in the amounts of both catalysts and dialkylzinc reagents to be loaded. Georg Thieme Verlag Stuttgart.
A boron-oxygen transborylation strategy for a catalytic midland reduction
Nicholson, Kieran,Dunne, Joanne,DaBell, Peter,Garcia, Alexander Beaton,Bage, Andrew D.,Docherty, Jamie H.,Hunt, Thomas A.,Langer, Thomas,Thomas, Stephen P.
, p. 2034 - 2040 (2021/02/20)
The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron.oxygen transb
Use of the 2-Pyridinesulfonyloxy Leaving Group for the Fast Copper-Catalyzed Coupling Reaction at Secondary Alkyl Carbons with Grignard Reagents
Shinohara, Riku,Morita, Masao,Ogawa, Narihito,Kobayashi, Yuichi
supporting information, p. 3247 - 3251 (2019/05/10)
Investigation of the copper-catalyzed coupling reaction of 2-pyridinesulfonates with Grignard reagents revealed that reactions with catalytic Cu(OTf)2 were completed in 40 min. The results differed from those of the previous CuI-catalyzed reactions of tosylates in the presence of additives (LiOMe and TMEDA) for 12-24 h. It was shown that the preferred coordination of the leaving group to the reagents accelerated the reaction. Successful reagents were MeMgCl and other RMgX. Complete inversion was established.
Axially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes
Sweetman, Brian A.,Guiry, Patrick J.
, p. 5567 - 5581 (2018/08/09)
The synthesis and resolution of new tridentate isoquinoline-derived ligands has been developed. The key steps in the synthetic sequence include successive, chemo-selective Suzuki-Miyaura cross-couplings of 1,3-dichloroisoquinoline with suitable arylboronic acids. The new ligands prepared in this manner were resolved either via molecular complexation with N-benzylcinchonidinium chloride as with 1-[3-(2-hydroxyphenyl)isoquinolin-1-yl]naphthalen-2-ol or via chromatographic separation of its epimeric camphorsulfonates as for 1,3-bis-(2-hydroxynaphthalen-1-yl)isoquinoline. 4-tert-Butyl-2-chloro-6-[1-(2-hydroxymethylnaphthalen-1-yl)isoquinolin-3-yl]phenol was resolved by chiral semi-preparative HPLC. The application of these ligands in the diethylzinc addition to aldehydes was investigated. In certain cases, the desired secondary alcohols were obtained in high yield with excellent enantiomeric excess (ee > 99%) at low catalyst loading (1 mol%).
