Carbohydrate-derived PSE acetals: controlled base-induced ring cleavage

Chéry, Florence; Cabianca, Elena; Tatibouët, Arnaud; Lucchi, Ottorino De; Rollin, Patrick

doi:10.1016/j.tet.2011.11.009

Cited by 7 publications

(4 citation statements)

References 19 publications

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“…In 2012, the group of Patrick Rollin demonstrated that PSE acetals can be opened using n-butyllithium (nBuLi) through a retro-Michael reaction, which may lead to two regioisomeric vinylsulfonyl ethers (Scheme 12). [71] There is no apparent rationale Scheme 12. nBuLi-mediated retro-Michael opening of PSE acetals on a furanose and mechanistic pathway. for the observed regioselectivity of the reaction, but it is thought to be fully dependent on the substrate.…”

Section: Reductive Methodsmentioning

confidence: 99%

“…Furthermore, tert-butyl ethers are highly uncommon protecting Scheme PSE acetals on pyranoses can be partially cleaved by strong bases, such as nBuLi. [71] A series of PSE acetals (179 and 182) was examined in the base-induced cleavage and revealed low regioselectivity profiles, with a slight preference for the 6-Oderivatives (Scheme 47). No differences were observed between cis-and trans-1,3-dioxanopyran systems.…”

Section: Reductive Methodsmentioning

confidence: 99%

“…PSE acetals are not only susceptible to SET mediated transformations, but can also be opened using organometallic bases. In 2012, the group of Patrick Rollin demonstrated that PSE acetals can be opened using n‐butyllithium ( n BuLi) through a retro‐Michael reaction, which may lead to two regioisomeric vinylsulfonyl ethers (Scheme ) . There is no apparent rationale for the observed regioselectivity of the reaction, but it is thought to be fully dependent on the substrate.…”

Section: Furansmentioning

confidence: 99%

“…PSE acetals on pyranoses can be partially cleaved by strong bases, such as n BuLi . A series of PSE acetals ( 179 and 182 ) was examined in the base‐induced cleavage and revealed low regioselectivity profiles, with a slight preference for the 6‐ O ‐derivatives (Scheme ).…”

Section: Pyransmentioning

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: Reductive Methodsmentioning

confidence: 99%

Section: Furansmentioning

confidence: 99%

Section: Pyransmentioning

confidence: 99%

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