Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to α,β,γ,δ-unsaturated sulfonic esters: controlling regioselectivity by rational selection of electron-withdrawing groups

Lu, Junzhu; Ye, Jinxing; Weng, Duan

doi:10.1039/c3cc46290k

Cited by 82 publications

(24 citation statements)

References 72 publications

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“…()] . High ee values like these have only been reported for electron‐rich substrates, such as enones, bis(enones), ketimines, and sulfonic esters, which have achieved ee values of greater than 95 %. Values of this magnitude are yet to be seen for other substrates.…”

Section: Selectivitymentioning

confidence: 99%

Challenges in Catalytic Hydrophosphination

Bange

Waterman

2016

Chemistry A European J

144

127

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Despite significant advances, metal-catalyzed hydrophosphination has ample room for discovery, growth, and development. Many of the key successes in metal-catalyzed hydrophosphination over the last decade have indicated what is needed and what is yet to come. Reactivity that is absent from the literature also speaks to the challenges in catalytic hydrophosphination. This Concept article discusses and highlights recent developments that address the ongoing challenges, and identifies areas in metal-catalyzed hydrophosphination that are underdeveloped. Advances in product selectivity, catalyst design, and both unsaturated and phosphine substrates illustrate the ongoing development of the field. Like all catalytic transformations, the benefits are realized through catalyst, ligand, and conditions, and consideration of those features are the route to a yet more efficient and broadly applicable reaction.

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Section: Selectivitymentioning

confidence: 99%

Challenges in Catalytic Hydrophosphination

Bange

Waterman

2016

Chemistry A European J

144

127

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“…76 The excellent enantioselectivity of these phospha-Michael reactions is the starting point for a useful route to the synthesis of chiral phosphine-oxazoline ligands. The phosphine sulfide (S)-160 (Table 20, In conclusion, Tables 18−20 report more than 70 examples of enantioselective phospha-Michael reactions, with different catalysts, different P(III) and P(V) nucleophiles, and a variety of 1-(1H-pyrrol-1-yl)prop-2-en-1-ones (1); in all cases, the enantioselectivity was >90% ee.…”

Section: All Of the Above Reactions Have Been Run With P(v) Reagents mentioning

confidence: 99%

Enantioselective Catalytic Reactions with N-Acyliden Penta-atomic Aza-heterocycles. Heterocycles as Masked Bricks To Build Chiral Scaffolds

2015

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“…(3)]. [15] High ee values like these have only been reported for electron-rich substrates, such as enones, [12,[15][16] bis(enones), [16b, 17] ketimines, [18] and sulfonice sters, [19] whichh ave achieved ee values of greater than 95 %. Values of this magnitude are yet to be seen for other substrates.…”

Section: Stereoselectivitymentioning

confidence: 99%