Lewis acid mediated asymmetric Diels–Alder reactions of chiral 2-phosphonoacrylates

Zhu, Jia‐Liang; Chen, Po-Erh; Huang, Hue-Wen

doi:10.1016/j.tetasy.2012.11.021

Cited by 8 publications

(1 citation statement)

References 54 publications

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“…To date, the most widely employed precursors for amino-Heck reactions are O -pentafluorobenzoyloximes, , which are proved to be superior to many other kinds of oximes, such as sulfonyl-, acetyl-, and benzoyloximes, in terms of reactivity, stability, and production of fewer undesired byproducts . In our continuation study on the cyclization reactions of phosphonyl compounds, − we previously demonstrated that a range of γ,δ-unsaturated diethylphosphinyloximes could cyclize smoothly in a 5- exo fashion under the catalysis of Pd(PPh 3 ) 4 in refluxing CH 3 CN with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), to afford substituted pyrroles or indoles in good to high yields . As compared with the acyloxime counterparts, these substrates also exhibited the unique regioselectivity in adopting a 6- endo pathway to produce pyridines under the different catalytic conditions .…”

Section: Introductionmentioning

confidence: 93%

Access to Functionalized Bicyclo[4,3,0]nonenes via Palladium-Catalyzed Oxidative Cyclization of 2-Allylcyclohexyl Oximes

Zhu

Shie

2014

J. Org. Chem.

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A new palladium-catalyzed oxidative cyclization process leading to the functionalized bicyclo[4,3,0]nonenes is serendipitously discovered during attempts to form aza-heterocycle by the amino-Heck reaction of trans-2-vinylclohexyl phosphinyloxime. Under the influence of Pd(dba)2/Et3N/1:1 N2-O2 (1:1, v/v) (Method A) or Pd(OAc)2/Et3N/O2 (Method B), the reactions afford the substituted cis-1-hydroxyl-8-formyl-bicyclo[4,3,0]non-8(9)-enes or bicycle[4,3,0]non-1(9)-en-8-ones in varying yields with the incorporation of molecular oxygen into the structures. The 5,6-bicyclic scaffold of these products is presumably derived from tandem double intramolecular cyclization followed by the ring-opening of an aza-palladium(II) tricyclic intermediate.

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Section: Introductionmentioning

confidence: 93%

Access to Functionalized Bicyclo[4,3,0]nonenes via Palladium-Catalyzed Oxidative Cyclization of 2-Allylcyclohexyl Oximes

Zhu

Shie

2014

J. Org. Chem.

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Addition Reactions: Cycloaddition

Dennis¹

2016

Organic Reaction Mechanisms · 2013

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Thermal Cyclization of Copper Carbenoid of α‐Dizao α‐Phosphorylacetate: Unexpected and Novel Access to Oxaphosphirane

Shie

Zhu

2015

J Chinese Chemical Soc

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Under the catalysis of Cu(OTf)2 in refluxing CH2Cl2, ethyl α‐dizao α‐(diethylphosphoryl)acetate was shown to undergo a new cyclization reaction to afford a pentacovalent oxaphosphirane product. The reaction is proposed to occur through the addition of the P=O double bond to the copper carbenoid, followed by the hydrolysis of the ylide intermediate. Our finding represents the first example on producing oxaphosphiranes from dizao phosphoryl compounds. On the other hand, the corresponding rhodium carbenoid displayed the different reactivity under the same thermal conditions, to produce the β‐propiolactone through the well‐recognized C‐H insertion pathway.

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Lewis acid mediated asymmetric Diels–Alder reactions of chiral 2-phosphonoacrylates

Cited by 8 publications

References 54 publications

Access to Functionalized Bicyclo[4,3,0]nonenes via Palladium-Catalyzed Oxidative Cyclization of 2-Allylcyclohexyl Oximes

Access to Functionalized Bicyclo[4,3,0]nonenes via Palladium-Catalyzed Oxidative Cyclization of 2-Allylcyclohexyl Oximes

Addition Reactions: Cycloaddition

Thermal Cyclization of Copper Carbenoid of α‐Dizao α‐Phosphorylacetate: Unexpected and Novel Access to Oxaphosphirane

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