Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyloxetanes with Formaldehyde

Xu, Hang; Khan, Sardaraz; Li, Hongfang; Wu, Xue; Zhang, Yong Jian

doi:10.1021/acs.orglett.8b03665

Cited by 44 publications

(15 citation statements)

References 65 publications

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“…For instance, the enantioselective [4+2] cycloaddition of vinyloxetanes with formaldehyde has proved to be an efficient method for the formation of enantiopure 1,3-dioxanes with a quaternary stereocenter ( Scheme 299 ). 731 …”

Section: Cyclization Reactions Via Pd-catalyzed Interceptive Asymmetric Allylic Substitutionmentioning

confidence: 99%

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

359

202

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This Review compiles the evolution, mechanistic understanding, and more recent advances in enantioselective Pd-catalyzed allylic substitution and decarboxylative and oxidative allylic substitutions. For each reaction, the catalytic data, as well as examples of their application to the synthesis of more complex molecules, are collected. Sections in which we discuss key mechanistic aspects for high selectivity and a comparison with other metals (with advantages and disadvantages) are also included. For Pd-catalyzed asymmetric allylic substitution, the catalytic data are grouped according to the type of nucleophile employed. Because of the prominent position of the use of stabilized carbon nucleophiles and heteronucleophiles, many chiral ligands have been developed. To better compare the results, they are presented grouped by ligand types. Pd-catalyzed asymmetric decarboxylative reactions are mainly promoted by PHOX or Trost ligands, which justifies organizing this section in chronological order. For asymmetric oxidative allylic substitution the results are grouped according to the type of nucleophile used.

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Section: Cyclization Reactions Via Pd-catalyzed Interceptive Asymmetric Allylic Substitutionmentioning

confidence: 99%

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

359

202

View full text Add to dashboard Cite

show abstract

“…In 2019, Zhang and coworkers successfully synthesized the 1,3‐dioxane 5 in high enantioselectivity (95 % ee ) through the asymmetric DC of cyclic carbonate 1 g with formaldehyde by using the palladium complex generated in situ from Pd 2 (dba) 3 ⋅CHCl 3 and chiral phosphoramidite L1 as a catalyst (Scheme 13). [7] …”

Section: π‐Allyl Palladium Bearing O‐nucleophilementioning

confidence: 99%

“… Palladium‐catalyzed decarboxylative [4+2] cycloaddition of 4‐vinyl‐1,3‐dioxan‐2‐one with formaldehyde [7] …”

Section: π‐Allyl Palladium Bearing O‐nucleophilementioning

confidence: 99%

“…In 2019, Zhang and coworkers successfully synthesized the 1,3-dioxane 5 in high enantioselectivity (95 % ee) through the asymmetric DC of cyclic carbonate 1 g with formaldehyde by using the palladium complex generated in situ from Pd 2 (dba) 3 •CHCl 3 and chiral phosphoramidite L1 as a catalyst (Scheme 13). [7] In 2020, Hou and coworkers disclosed a highly enantioselective decarboxylative [4 + 2] cycloadditions of 4-vinyl-1,3dioxan-2-ones 1 and electron-deficient alkenes 6 (Scheme 14). [8] By using chiral P,N-ligand L2, the reaction could afford tetrahydropyrans 7 bearing three continuous chiral centers in high yields (up to 99 %) with high diastereo-and enantioselectivities (up to 20 : 1 dr and 98 % ee).…”

Section: -Vinyl-13-dioxan-2-onesmentioning

confidence: 99%

“…Palladium-catalyzed decarboxylative [4 + 2] cycloaddition of 4vinyl-1,3-dioxan-2-one with formaldehyde. [7] Scheme 14. Palladium-catalyzed enantioselective DCs of 4-vinyl-1,3-dioxan-2-ones with electron-deficient alkenes.…”

Section: -Vinyl-13-dioxan-2-onesmentioning

confidence: 99%

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Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

You

Zhang

et al. 2022

ChemCatChem

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Palladium‐catalyzed decarboxylative cycloadditions have emerged as highly effective methods for constructing structurally diverse carbo‐ and heterocycles because of the formation of at least two carbon‐carbon or carbon‐heteroatom bonds in a single step. It is of great interest to chemists that this type of cycloaddition reactions possesses some special advantages such as high reactivity, exclusive regioselectivity, and good functional group compatibility. Based on these qualities, palladium‐catalyzed decarboxylative cycloadditions present strong ability in synthetic chemistry and have been flourished especially in the last five years. In this review, the achievements in palladium‐catalyzed decarboxylative cycloadditions involving cyclic carbonates, carbamates, and lactones for accessing oxacyclo‐, azacyclo‐ and carbocyclic compounds are addressed. Mechanistic insights and some synthetic applications toward the synthesis of natural products are discussed. The challenges and opportunities of this field are also outlined.

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Formaldehyde asC1 Synthon in Organic Synthesis

Li¹,

Wu²

2022

The Chemical Transformations of C1 Compounds

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Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyloxetanes with Formaldehyde

Cited by 44 publications

References 65 publications

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

Formaldehyde asC1 Synthon in Organic Synthesis

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