Palladium‐Catalyzed Three‐Component Tandem Reaction for One‐pot Highly Stereoselective Synthesis of (<i>Z</i>)‐<i>α</i>‐Hydroxymethyl Allylic Sulfones

Hou, Yunlei; Shen, Qi; Li, Zefei; Chen, Shaowei; Zhao, Yanfang; Qin, Mingze; Gong, Ping

doi:10.1002/adsc.201701011

Cited by 27 publications

(19 citation statements)

References 51 publications

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“…The Scheme has shown several metal‐catalyzed regioselective additions of sulfonyl hydrazides to unsaturated bonds via formation of π‐metal‐allyl species . Allenes and in situ generated π‐allylpalladium intermediates from allylic amines were tested in this decade. Lu and co‐workers employed arylpropyne compounds as the precursor of linear allenes (Eq.…”

Section: Rso2‐[metal] Intermediatesmentioning

confidence: 99%

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Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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Section: Rso2‐[metal] Intermediatesmentioning

confidence: 99%

“…52‐2). Gong and co‐workers designed a three‐component reaction for synthesis of ( Z )‐α‐hydroxymethyl allylic sulfones (Eq. 52‐3).…”

Section: Rso2‐[metal] Intermediatesmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…Remarkably, alkylvinylethylene carbonates gave the corresponding aliphatic products (41-45) as exclusively cis-isomers in good yields. This represents a complementary method to the recent elegant publication of Gong et al, [16] who reported a palladiumcatalyzed three-component tandem reaction of allenes with aryl iodides and sulfonyl hydrazides. However, using their protocol, aliphatic sulfonyl hydrazides and aliphatic iodides failed to give (Z)-allylic sulfones.…”

Section: Direct Synthesis Of Substituted (Z)-allylic Sulfones By Pallmentioning

confidence: 90%

“…Interestingly, the desired product was obtained in the presence of Pd(0) ( Table 1, entries 9 and 10). Other parameters, such as catalyst loading, ligand, atmosphere, and sodium benzenesulfinate equivalents, were also tested, with optimal conditions eventually determined (see Table 1, entry 16). Reactions conducted in DCM, CH 3 CN, toluene, and MeOH resulted in diminished yields, while using THF afforded a lower Z/E ratio (Table 1, entries 11-15).…”

Section: Direct Synthesis Of Substituted (Z)-allylic Sulfones By Pallmentioning

confidence: 99%

Direct Synthesis of Substituted (Z)‐Allylic Sulfones by Palladium‐Catalyzed Sulfonylation of Vinylethylene Carbonates with Sodium Sulfinates

Huang

Fang

et al. 2019

ChemCatChem

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A palladium‐catalyzed highly stereoselective sulfonylation of vinylethylene carbonates for the precise synthesis of structurally diverse (Z)‐allylic sulfones was achieved with excellent regioselectivity and stereoselectivity (Z/E ratio, up to 99 : 1). This protocol used inexpensive sodium sulfinates as sulfonyl sources to construct valuable (Z)‐allylic sulfones in good to excellent yields. The controlling experiment suggested that the hydroxyl proton came from the α‐hydrogen of sulfone group through 1, 5‐H shift.

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“…Interestingly, allene 476 lacking hydroxyl unit, failed to yield the corresponding substituted alkene 477 , supporting the proposed mechanistic pathway and the coordinative role of the OH group in the reported transformation ( Scheme 82 , reaction b). 307 − 309 …”

Section: Synthetic Utilitymentioning

confidence: 99%

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

2021

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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.

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Palladium‐Catalyzed Three‐Component Tandem Reaction for One‐pot Highly Stereoselective Synthesis of (Z)‐α‐Hydroxymethyl Allylic Sulfones

Cited by 27 publications

References 51 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Direct Synthesis of Substituted (Z)‐Allylic Sulfones by Palladium‐Catalyzed Sulfonylation of Vinylethylene Carbonates with Sodium Sulfinates

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

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