Palladium‐Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit

Li, Qiankun; Fu, Chunling; Ma, Shengming

doi:10.1002/ange.201402647

Cited by 13 publications

(1 citation statement)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hamada performed the same palladium-catalyzed reaction between allenyl acetates 636 and malonates but replacing Trost ligand with ( S , R P )-DIAPHOXs, a chiral nonracemic diaminophosphine oxide, which results in the formation of axially chiral allenes ( R )- 637 in good yields with up to 99% ee . 370 The above-mentioned palladium-catalyzed amination of allenyl phosphonates, 371 and the addition of malonates to allenyl acetates, 372 , 373 have also been explored by Ma and collaborators in the context of achieving central as much as axial chirality from racemic allenes. The same research group has deeply investigated different allenyl esters in the presence of various nucleophiles yielding substituted allenes exhibiting both types of chirality.…”

Section: Synthetic Utilitymentioning

confidence: 99%

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

2021

View full text Add to dashboard Cite

The allene functionality has participated in one of the most exciting voyages in organic chemistry, from chemical curiosities to a recurring building block in modern organic chemistry. In the last decades, a special kind of allene, namely, allenol, has emerged. Allenols, formed by an allene moiety and a hydroxyl functional group with diverse connectivity, have become common building blocks for the synthesis of a wide range of structures and frequent motif in naturally occurring systems. The synergistic effect of the allene and hydroxyl functional groups enables allenols to be considered as a unique and sole functionality exhibiting a special reactivity. This Review summarizes the most significant contributions to the chemistry of allenols that appeared during the past decade, with emphasis on their synthesis, reactivity, and occurrence in natural products.

show abstract

Section: Synthetic Utilitymentioning

confidence: 99%

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

2021

View full text Add to dashboard Cite

show abstract

Rhodium‐Catalyzed Asymmetric Allenylation of Sulfonylimines and Application to the Stereospecific Allylic Allenylation

et al. 2016

View full text Add to dashboard Cite

Ther hodium-catalyzeda symmetric allenylation of sulfonylimines is disclosedp roviding silyl homoallenylamide productsi nu pt o9 9:1 er. Through subsequent activation of the C À Nb ondo f the silyl homoallenyl sulfonamide,p alladium-catalyzed stereospecific allylic allenylation could be achieved giving C À Cb ond formation with high chirality transfer.T he synthetic utility of both the silyl homoallenyl sulfonamides andt he silyl homoallenyl malonatesasb is(nucleophiles) is demonstrated.

show abstract

Regioselectivity Switch in Palladium‐Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross‐Coupling

Luo

Deng

et al. 2019

Angewandte Chemie

View full text Add to dashboard Cite

The first Pd-catalyzed asymmetric allenylic [4+ +1] cycloaddition was successfully developed. Alternatively,tuning the Pd catalyst switched the reactivity toward an unprecedented [4+ +3] cycloaddition/cross-coupling. Ligands play av ital role in controlling the reaction pathway,a llowing highly selective access to different products from identical substrates.B iological evaluation of the obtained compounds led to the discovery of new antitumor targets.Apossible mechanism is proposed, suggesting two interesting catalytic cycles for the cycloaddition with palladium-butadienyls.T his study also demonstrated the potential and utility of allenic esters as 1,4-biselectrophiles and C 4 synthons for participating in cycloaddition reactions.

show abstract

Palladium‐Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit

Cited by 13 publications

References 39 publications

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Rhodium‐Catalyzed Asymmetric Allenylation of Sulfonylimines and Application to the Stereospecific Allylic Allenylation

Regioselectivity Switch in Palladium‐Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross‐Coupling

Contact Info

Product

Resources

About