Modified BINOL Ligands in Asymmetric Catalysis

Chen, Yu; Yekta, Shahla; Yudin, Andrei K.

doi:10.1021/cr020025b

Cited by 921 publications

(365 citation statements)

References 244 publications

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“…4 The first ligand examined was a BINOL derivative with a 9-anthracenyl substituent in the 3 and 3′ positions. The 9-anthracenyl group combines a significant electron-withdrawing ability with significant steric bulk.…”

Section: Synthesis Of Electron Withdrawing Binaphthols and Biphenolsmentioning

confidence: 99%

“…After stirring the mixture for 12 h at 22 °C, it was cooled to 0 °C and water was added. The mixture was extracted with dichloromethane, the dichloromethane solution was dried over MgSO 4 , and the solvent was evaporated. Flash column chromatography (silica gel, toluene/ hexane/ethyl acetate 25:25:1) gave 3,3′-bis- (9) …”

Section: 3′-bis-(9-anthracenyl)-binol (H 2 [Binaph Anth ])mentioning

confidence: 99%

“…The mixture was extracted with chloroform. The chloroform solution was separated and dried over MgSO 4 …”

Section: 3′-bis(pentafluorophenyl)-binol (H 2 [Binaph C6f5 ])mentioning

confidence: 99%

“…The mixture was extracted with dichloromethane. The dichloromethane layer was dried over MgSO 4 , and the solvent evaporated in vacuo. Flash column chromatography (silica gel, hexane/ethyl acetate 30:1) gave 3,3′-bis (3,5- …”

Section: 3′-bis(35-bis(trifluoromethyl)phenyl)-binol (H 2 [Binaph mentioning

confidence: 99%

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Molybdenum Imido Alkylidene Metathesis Catalysts That Contain Electron-Withdrawing Biphenolates or Binaphtholates

et al. 2007

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We have prepared new Mo(NR)(CHCMe 2 Ph)(diolate) complexes (R = 2,6-i-Pr 2 C 6 H 3 , 2,6-Me 2 C 6 H 3 , 1-Adamantyl, or 2-CF 3 C 6 H 4 ) that contain relatively electron-withdrawing binaphtholate (3,3′-bis-(9-anthracenyl), 3,3′-bispentafluorophenyl, or 3,3′-bis(3,5-bis(trifluoromethyl)phenyl) or biphenolate (3,3′-di-tert-butyl-5,5′-bistrifluoromethyl-6,6′-dimethyl-1,1′-biphenyl-2,2′-diolate) ligands. We also have prepared new monomeric Mo(NR)(CHCMe 2 Ph)(2,5-dimethylpyrrolide) 2 complexes and have treated them with biphenols or binaphthols in order to prepare several Mo(NR) (CHCMe 2 Ph)(diolate) species. In one case the new Mo(NR)(CHCMe 2 Ph)(diolate) complexes could be prepared only through reaction of a binaphthol [3,3′-bis(pentafluorophenyl)binaphthol] with a bis (2,5-dimethylpyrrolide) complex. The pyrrolide approach can be employed either to isolate catalysts on a preparative scale or to generate catalysts in situ. Several simple preliminary ring-closing metathesis reactions show that the new complexes are catalytically competent.

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Section: Synthesis Of Electron Withdrawing Binaphthols and Biphenolsmentioning

confidence: 99%

Section: 3′-bis-(9-anthracenyl)-binol (H 2 [Binaph Anth ])mentioning

confidence: 99%

“…The mixture was extracted with chloroform. The chloroform solution was separated and dried over MgSO 4 …”

Section: 3′-bis(pentafluorophenyl)-binol (H 2 [Binaph C6f5 ])mentioning

confidence: 99%

Section: 3′-bis(35-bis(trifluoromethyl)phenyl)-binol (H 2 [Binaph mentioning

confidence: 99%

See 2 more Smart Citations

Molybdenum Imido Alkylidene Metathesis Catalysts That Contain Electron-Withdrawing Biphenolates or Binaphtholates

et al. 2007

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show abstract

“…The addition of silyl enol ether 266 to hydrazone 265 occurred in 66% yield and 86% ee. 78 Akin to the Diels-Alder reaction described above, a screen of hydrobenzoin derivatives could lead to results that improve upon this enantioselectivity and lead to an efficient and economical route to β-aminocarbonyls. Thus, building on considerable precedent related to the use of 3,3'-substituted BINOL as an asymmetric catalyst, chiral hydrobenzoin derivatives could be screened in these reactions to see if there is a similar increase in enantioselectivity.…”

Section: Resultsmentioning

confidence: 99%