- Palladium-catalyzed aerobic oxidative coupling of enantioenriched primary allylic amines with sulfonyl hydrazides leading to optically active allylic sulfones
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A range of highly enantioenriched primary allylic amines underwent palladium-catalyzed oxidative coupling with sulfonyl hydrazides open to air at room temperature to give structurally diverse allylic sulfones in moderate to excellent yields with excellent retention of ee. This journal is the Partner Organisations 2014.
- Wang, Ting-Ting,Wang, Fu-Xiang,Yang, Fu-Lai,Tian, Shi-Kai
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supporting information
p. 3802 - 3805
(2014/04/03)
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- Efficient palladium catalysts containing original imidazolium-tagged chiral diamidophosphite ligands for asymmetric allylic substitutions in neat ionic liquid
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New imidazolium-tagged chiral diamidophosphite ligands, (S,S)-a and (R)-b, derived from (S,S)-N,N′-dibenzyl-1,2-cyclohexanediamine and (R)-N,N′-dimethyl-1,1′-binaphthyl-2,2′-diamine, respectively, and the corresponding palladium allylic complexes of general formula [PdCl(η3-2-Me-C3H4)(κ1P-L) ]BF4 (1a,b) and [Pd(η3-2-Me-C3H 4)(κ1P-L)2](BF4)3 (2a,b) were synthesized and fully characterized, including the X-ray crystal structure for 1b. These original Pd/L catalytic systems were applied in asymmetric allylic alkylation, amination, and sulfonylation using rac-3-acetoxy-1,3-diphenyl-1-propene as a substrate in neat ionic liquids, [bmim][PF6] and [Pyr][NTf2]. The best results in terms of enantioselectivity were obtained with the catalytic precursor 1b in [Pyr][NTf2]. The catalytic phase containing 1b for the allylic amination could be recycled up to six times without significant loss of asymmetric induction.
- Bravo, Maritza J.,Favier, Isabelle,Saffon, Nathalie,Ceder, Rosa M.,Muller, Guillermo,Gomez, Montserrat,Rocamora, Merce
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p. 771 - 779
(2014/03/21)
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- Palladium catalyzed asymmetric sulfonylation mediated chiral β-hydroxy- and β-(o-diphenylphosphino)benzoyloxy (o-diphenyl phosphino)benzamides
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The palladium catalyzed asymmetric allylic sulfonylation reaction has been investigated employing β-hydroxy- and β-(o-diphenylphosphino) benzoyloxy (o-diphenyl phosphino)benzamides as chiral, non-racemic ligands. The bisphosphine β-benzoyloxybenzamide ligands proved to be the best ligands for this process. Competitive transition states for the (1S,2R)-norephedrine derived ligand 14 are compared and a rationale is provided for the observed enantioselectivities.
- Wolfe, Jesse A.,Hitchcock, Shawn R.
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scheme or table
p. 2690 - 2695
(2011/03/17)
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- An expeditious entry to benzylic and allylic sulfones through byproduct-catalyzed reaction of alcohols with sulfinyl chlorides
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(Chemical Equation Presented) In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellen
- Li, Hai-Hua,Dong, De-Jun,Jin, Yin-Huan,Tian, Shi-Kai
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supporting information; experimental part
p. 9501 - 9504
(2010/03/04)
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