Copper-catalyzed domino reactions: conjugate alkylative aldol addition/lactonization of α,β-unsaturated diesters

Li, Zhiqiang; Li, Ruirui; Gan, Miaomiao; Jiang, Lan; Li, Zhengning

doi:10.1016/j.tetlet.2015.08.031

Cited by 8 publications

(2 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2015, Shi and co-workers devised a copper-catalyzed domino conjugate alkylative aldol addition/lactonization of α,β-unsaturated diester 92 with carbonyl derivatives 91 (ketones or aldehydes) and diethyl zinc. 47 High yields were achieved, wherein diethyl zinc was employed as an alkyl Michael donor in the presence of 1 mol% CuF(PPh 3 ) 3 •2MeOH as catalyst. In the case of maleate, diethyl zinc acted as a reducing reagent that provided a hydride for Michael addition and thus afforded the corresponding lactones following the conjugate reduction-induced domino reaction (Scheme 25, B).…”

Section: Alkylative Spirolactonization Of αβ-Unsaturated Esters (Metmentioning

confidence: 99%

Transition-Metal-Catalyzed Synthesis of Spirolactones

2017

View full text Add to dashboard Cite

Spiranoid lactone structures can frequently be observed as scaffold segments of various biochemical compounds and drugs of natural origin. Examples of these structures have been identified among terpenoids, alkaloids, steroids, carbohydrates, and many other natural products. Such a broad natural diversity and biological activity allows a wide spectrum of these systems to be attractive targets for synthetic and medicinal chemists. Covering a broad spectrum of recognized approaches toward the design of spirolactones established over the past several decades, this review focuses on transition-metal-catalyzed synthesis, which is the most prominent methodology reported to date.1 Introduction2 Patterned Approaches2.1 Cyclocarbonylation2.2 Hydroalkylation/Arylation of Hydroxy α,β-Acetylenic Esters2.3 [2+2+2]-Cyclotrimerization: Rapid Access to Spirobenzofuranone Scaffolds2.4 Cyclization of Allenoic Acids/Allenoates2.5 Cycloisomerization–Oxidation of Homopropargyl Alcohols2.6 Hydroalkoxylation of Alkynoic or Alkenoic Acids2.7 C–H Carbonylation: Access to Spirobenzofuranone and Spiroisochromanone Derivatives2.8 Alkylative Spirolactonization of α,β-Unsaturated Esters2.9 Olefin Ring-Closing Metathesis2.10 Reductive Opening of Epoxides2.11 Intramolecular C–H Insertion3 Nonpatterned Approaches3.1 Azomethine Ylide Cycloaddition3.2 Hydrohydroxyalkylation of Vicinal Diols3.3 Photoredox Catalysis: C-Alkylation of Alcohols3.4 Carbonylative Spirolactonization of Hydroxycyclopropanols3.5 Copper-Catalyzed Alkylation of β-Keto Esters4 Conclusion

show abstract

Section: Alkylative Spirolactonization Of αβ-Unsaturated Esters (Metmentioning

confidence: 99%

Transition-Metal-Catalyzed Synthesis of Spirolactones

2017

View full text Add to dashboard Cite

show abstract

“…[4] In the presence of aldehydes,s ubsequent aldolization can take place and domino 1,4-addition-aldol condensation reactions have been implemented for N-enoyloxazolidinones [5] and a,b-unsaturated esters. [6,7] These protocols offer somea ttractive features:t hey proceedi nt he absence of any transition metal catalyst and under mild conditions; [8] all the reactive partners can be introduced from the start since dialkylzinc reagents do not react directly with aldehydes and the radicalc haractero ft he process permits the use of alkyl iodides as partnerso ft he three-component reaction. [5-7, 9, 10] However,i mplementation of thesep rotocols in synthesis has so far been hampered by the lack of general ande fficient asymmetricv ariants.T he use of Evanstype oxazolidinone chiral auxiliaries were considered for Nenoyloxazolidinones buth ad limited success: [5a] the levels of chiral induction where up to 88:12, but the relative configuration between the two adjacent stereocenters created during the aldol condensation could not be controlled (Scheme 1, top).We have recently demonstrated that chiral N-phenylglycinolderived 2,4-disubstituted oxazolidines are excellentc hiral auxiliaries for the asymmetric condensation of amide-stabilized sulfonium ylides with aldehydes.…”

mentioning

confidence: 99%

Asymmetric Tandem Conjugate Addition–Aldol Condensation with N‐Acryloyloxazolidines Derived from 2‐Phenylglycinol

Zelocualtecatl-Montiel

García-Álvarez

Juárez

et al. 2016

Asian J Org Chem

View full text Add to dashboard Cite

The tandem 1,4‐addition–aldol condensation reaction of diethylzinc, α,β‐unsaturated chiral enantiopure oxazolidines derived from 2‐phenylglycinol, and carbonyl compounds is disclosed. The reaction proceeds through a radical‐polar crossover mechanism involving the aldol condensation of a trisubstituted zinc enolate through a Zimmerman–Traxler transition state. Installation of a 2‐pyridine moiety at the hemiaminal position of the chiral auxiliary allows obtaining both excellent asymmetric induction and diastereoselectivity (up to >90 % de). The developed protocol is suitable for aromatic and aliphatic aldehydes, as well as ketones.

show abstract

Copper, fluorotris(triphenylphosphine)-; Copper, fluorotris(triphenylphosphine) with methanol (1:2); Copper, fluorotris(triphenylphosphine) with ethanol (1:2)

Riant

Rasson

2017

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

Copper-catalyzed domino reactions: conjugate alkylative aldol addition/lactonization of α,β-unsaturated diesters

Cited by 8 publications

References 52 publications

Transition-Metal-Catalyzed Synthesis of Spirolactones

Transition-Metal-Catalyzed Synthesis of Spirolactones

Asymmetric Tandem Conjugate Addition–Aldol Condensation with N‐Acryloyloxazolidines Derived from 2‐Phenylglycinol

Copper, fluorotris(triphenylphosphine)-; Copper, fluorotris(triphenylphosphine) with methanol (1:2); Copper, fluorotris(triphenylphosphine) with ethanol (1:2)

Contact Info

Product

Resources

About