2011
DOI: 10.1021/ja2066829
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An Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters

Abstract: In transition-metal catalyzed, asymmetric α-arylation of carbonyl compounds, formation of tertiary centers with high enantioselectivity is a longstanding problem, due to easy enolization of the monoarylation products. Herein, we report such examples using a palladium catalyst supported by a new, (R)-H(8)-BINOL-derived monophosphine. Silyl ketene acetals, together with a weakly basic activator, were used as equivalents of ester anions, and they reacted smoothly with aryl triflates in excellent enantiomeric exce… Show more

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Cited by 118 publications
(67 citation statements)
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“…14 We have also developed a catalytic method 15 for direct oxidation of enantiomerically enriched alkenyl–B(pin) products to carboxylic acids (Scheme 6). 16 Enantioselective synthesis of nonsteroidal anti-inflammatory agent ( S )-naproxen was carried out on 2.0 mmol scale with 1.0 mol % of 6b , affording the acid in 75% overall yield and 95:5 er (94% es).…”
mentioning
confidence: 99%
“…14 We have also developed a catalytic method 15 for direct oxidation of enantiomerically enriched alkenyl–B(pin) products to carboxylic acids (Scheme 6). 16 Enantioselective synthesis of nonsteroidal anti-inflammatory agent ( S )-naproxen was carried out on 2.0 mmol scale with 1.0 mol % of 6b , affording the acid in 75% overall yield and 95:5 er (94% es).…”
mentioning
confidence: 99%
“…In a continuation of their recent work on palladium-catalyzed arylation of esters, 31 Zhou and coworkers described the synthesis of two new chiral phosphines that enable the first general method for asymmetrical a-arylation of lactones to produce tertiary stereogenic centers with high enantioselectivity (Scheme 17). 32 Various aromatic triflates were coupled to diverse lactones, affording the expected products in excellent yields and selectivities.…”
Section: Scheme 13mentioning
confidence: 99%
“…Nevertheless, asymmetric arylation to generate less-substituted centres is possible (Scheme 2.143). 173 The use of silyl enol ethers as enolate precursors allowed the avoidance of strongly basic conditions. A hard but mildly basic nucleophile, acetate, was included to liberate the enolate.…”
Section: Enolate and Phenoxide Couplingmentioning
confidence: 99%