Phenylsulfonylethylidene (PSE) acetals as atypical carbohydrate-protective groups

Chéry, Florence; Rollin, Patrick; Lucchi, Ottorino De; Cossu, Sergio

doi:10.1016/s0040-4039(00)00199-4

Cited by 23 publications

(6 citation statements)

References 6 publications

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“…[68] PSE acetals were introduced by Chéry et al in 2000, and have proven to be useful protecting groups in carbohydrate chemistry. [69,70] Their ring opening largely proceeds via a radical mechanism and starts with the formation of a primary radical under the elimination of a phenylsulfinate salt. Depending on the exact pathway and moment of scavenging of the radical, three products can be expected (Scheme 11).…”

Section: Reductive Methodsmentioning

confidence: 99%

“…The only known examples of single electron transfer (SET) mediated transformations involve the opening of 2‐phenylsulfonylethylidene (PSE) acetals . PSE acetals were introduced by Chéry et al in 2000, and have proven to be useful protecting groups in carbohydrate chemistry , . Their ring opening largely proceeds via a radical mechanism and starts with the formation of a primary radical under the elimination of a phenylsulfinate salt.…”

Section: Furansmentioning

confidence: 99%

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Regioselective Ring Opening of 1,3‐Dioxane‐Type Acetals in Carbohydrates

et al. 2018

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The (regio)selective manipulation of hydroxyl groups in carbohydrates has been a long‐standing challenge in (bio)organic chemistry and continues to trigger the creative minds of many chemists. Among the various strategies that have been developed to address these issues, mostly relying on multistep procedures involving the use of protecting groups, the regioselective ring opening of 1,3‐dioxane‐type acetals has emerged as a powerful tool. Since the first papers on this subject appeared in the 1960s, a large variety in both acetal types and reagents for their partial cleavage has come to the fore. This review aims to give an overview of the different carbohydrate‐derived ring systems, ranging from four‐ to seven‐membered rings, on which regioselective ring‐openings have been performed, along with the appropriate reagents and combinations thereof. The transformations on 1,3‐dioxane acetals fit in a larger group of ring opening reactions of structurally related cyclic functional groups, including 1,3‐dioxolanes, 1,3‐oxathianes, orthoesters, cyclic carbonates and silylene acetals, which will not be discussed in this review.

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Section: Reductive Methodsmentioning

confidence: 99%

Section: Furansmentioning

confidence: 99%

Regioselective Ring Opening of 1,3‐Dioxane‐Type Acetals in Carbohydrates

et al. 2018

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“…PSE acetals are notable because introduction is via reaction of the diol with 1,2-bis(phenylsulfonyl)ethylene under basic (NaH or Bu t OK) conditions via a double Michael addition pathway. 67 PSE acetals are highly acid resistant but can be removed reductively using LiAlH 4 in Et 2 O. Boc-and Moc-ethylidene acetals are introduced onto 1,2-diols by a similar strategy using the appropriate alkyl propynoates in the presence of DMAP. 68 These acetals are also stable to acid-catalysed hydrolysis or methanolysis but can be deprotected by treatment with pyrrolidine (5.0 equiv.)…”

Section: Methodsmentioning

confidence: 99%

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Spivey

Srikaran

2001

Annu. Rep. Prog. Chem., Sect. B

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Another excellent and comprehensive 'update' review of protecting group (PG) strategies in organic synthesis has appeared this year. 1 Additionally, a focused review of advances in glycopolymer synthesis highlighting advances in PG/activating group methodology has been published. 2 Furthermore, the role of molecularly imprinted polymers in synthetic chemistry has been overviewed, including their use for directing regioselective acylation of polyhydroxysteroids. 3

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“…Phenylsulfonylethylidene (PSE) acetals have recently been reported as a new protecting group for diols in carbohydrate chemistry. 184 The group is introduced by an additionelimination-addition to 1,2-bis(sulfonyl)ethene (Scheme 111).…”

Section: Functionalised Sulfonesmentioning

confidence: 99%