2016
DOI: 10.1002/anie.201604182
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Abstract: Copper-catalyzed enantioselective propargylation of indoles with propargylic esters and sequential Huisgen cycloaddition with azides lead to the construction of chiral triarylmethanes, bearing a quaternary carbon center, with high to excellent enantioselectivities. The result described herein can be used in the enantioselective preparation of a tetraarylmethane.

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Cited by 112 publications
(39 citation statements)
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References 97 publications
(28 reference statements)
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“…Figure 1 b indicates that electron-rich phosphines are superior to electron-deficient phosphines possibly because electron-rich phosphine can facilitate the cleavage of the propargylic C–O bond when Cu-2 is converted to Cu-3 . Unlike other copper-catalyzed propargylation methods performed in aprotic solvents, 25 29 polydentate ligands did not accelerate the reaction in water in this study. Therefore, the copper-catalyzed propargylic C–O bond cleavage in water requires different ligand design principles.…”
Section: Results and Discussioncontrasting
confidence: 77%
“…Figure 1 b indicates that electron-rich phosphines are superior to electron-deficient phosphines possibly because electron-rich phosphine can facilitate the cleavage of the propargylic C–O bond when Cu-2 is converted to Cu-3 . Unlike other copper-catalyzed propargylation methods performed in aprotic solvents, 25 29 polydentate ligands did not accelerate the reaction in water in this study. Therefore, the copper-catalyzed propargylic C–O bond cleavage in water requires different ligand design principles.…”
Section: Results and Discussioncontrasting
confidence: 77%
“…77 The reaction proceeded under mild reaction conditions with high efficiency and excellent regioselectivity. Low yields were only observed when other conventional diamine ligands (111)(112)(113)(114)(115)(116)(117) were used along with the nickel catalyst, Fig. 3.…”
Section: Nickel Derived Catalystsmentioning
confidence: 99%
“…Nishibayashi and co-workers in the year 2016 developed a copper-catalyzed enantioselective propargylation of indoles 61 with propargylic esters 185, Scheme 81. 111 Treatment of 1,1,1-triuoro-2-phenylbut-3-yn-2-yl per-uorobenzoate 185 with indole 61 in the presence of 5 mol% of CuOTf$1/2C 6 H 6 and 10 mol% of (4S,5R)-diPh-Pybox 187a and N,N-diisopropylethylamine in methanol at room temperature for 1 hour furnished the desired propargyl substituted product 186 in 41% yield with 47% ee. Propargylic esters such as acetate and tert-butyl carbonate were unable to react under this reaction condition.…”
Section: Copper Derived Catalystsmentioning
confidence: 99%
“…Nishibayashi and co-workers developed copper catalyzed enantioselectivep ropargylationo fi ndoles with propargylic esters followed by Huisgen 1, 3-dipolarc ycloaddition with azides for the enantioselective synthesis of triarylmethanes containing quaternary stereocenters (Scheme 49). [82] With the use of (4S, 5R)-diPh-Pybox (35) as the chiral ligand high yields and enantioselectivity can be achieved (up to 86 %y ield and 97 % ee). The authors could further extend this methodology for the enantioselective synthesis of tetraaryl methanes.…”
Section: Metal Catalysismentioning
confidence: 99%