2004
DOI: 10.1002/anie.200460335
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Abstract: Excellent yields and enantioselectivies are attained in the synthesis of 3‐alkyl‐3‐aryl oxindoles based on the Pd‐catalyzed asymmetric allylic alkylation (AAA) reaction. This approach utilizes a nonbasic hydroxylic additive in the transformation of 3‐aryl oxindoles into complex, synthetically valuable oxindoles (see scheme).

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Cited by 209 publications
(50 citation statements)
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“…Indeed, the Pd catalyzed AAA proceeds to generate the quaternary stereocenter using the anthracenyl derived ligand L A as the preferred ligand (eq 77). 78 The use of the atom economical version involving generation of the π-allyl species via protonation of an allene also gave excellent results (eq 78). 49,79 Interestingly, with 3,3-disubstituted allylating agents, the regioselectivity can be controlled to direct C-C bond formation to the disubstituted terminus of the π-allyl unit (eq 79).…”
Section: Enantioselectivitymentioning
confidence: 99%
“…Indeed, the Pd catalyzed AAA proceeds to generate the quaternary stereocenter using the anthracenyl derived ligand L A as the preferred ligand (eq 77). 78 The use of the atom economical version involving generation of the π-allyl species via protonation of an allene also gave excellent results (eq 78). 49,79 Interestingly, with 3,3-disubstituted allylating agents, the regioselectivity can be controlled to direct C-C bond formation to the disubstituted terminus of the π-allyl unit (eq 79).…”
Section: Enantioselectivitymentioning
confidence: 99%
“…18 Standard conditions of Tsuji–Trost type allylation (Pd–allyl dimer catalyst, P-ligand, and base) applied toward 11j proceeded at 0 °C, and full conversion was achieved in 30 min resulting in 93% yield of 13j (same relative stereochemistry observed in Claisen rearrangement, confirmed by NMR). 19,20 Pyrrolone 13h could also be isolated as a single diastereomer in 95% yield after isolation and purification via this approach.…”
mentioning
confidence: 99%
“…Method 2: Following the method of Trost et al, 27 to a stirred solution of 13 (6.07 g, 21.8 mmol) in anhydrous CH 2 Cl 2 (200 mL) was added Hü nig's base (11.4 mL, 65.3 mmol) and thionyl chloride (1.91 mL, 26.1 mmol) and the resulting solution stirred for 25 min. After this time, the reaction mixture was poured into satd aq NaHCO 3 solution (100 mL) and extracted with Et 2 O (100 mLÂ3).…”
Section: General Procedures B: Dihydroxylation With Osomentioning
confidence: 99%