A General and Diastereoselective Route to Five‐Membered Carbocycles and Heterocycles from Acyclic Vinyl Sulfone‐Modified Carbohydrates

Atta, Ananta Kumar; Pathak, Tanmaya

doi:10.1002/ejoc.200900957

Cited by 10 publications

(1 citation statement)

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“…Recently, a review on the synthesis of pyrrolidine-containing iminosugars has been published in which substitution reactions and organometallic additions to nitrones and cyclic imines were the most used methods, including the harnessing of sulfone-group reactivity. Domino reactions are highly appealing for the synthesis of biologically active compounds , because they enable the formation of elaborated products in a step-economy manner with the avoidance of the often tedious isolation of synthesis intermediates. In this regard, we have developed a method for the synthesis of chiral polyhydroxylated pyrrolidines by means of a domino elimination/imine addition or elimination/Michael addition, which is herein documented.…”

Section: Introductionmentioning

confidence: 99%

Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral Pyrrolidines

Flores¹,

García‐García

Garrido³

et al. 2013

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral Pyrrolidines

Flores¹,

García‐García

Garrido³

et al. 2013

J. Org. Chem.

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Vinyl Selenones Derived from d‐Fructose: A New Platform for Fructochemistry

2016

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d-Fructose, an inexpensive biomass precursor available on al arge scale, has been used for the generation of enantiomerically pure chemical entities. Construction of vinyl selenone moieties on cyclic skeletons of d-fructose led to the highly reactive synthetic intermediates comprisingo f an electron-deficient double bond along with an excellent leaving group. Reactions of these Michael acceptors with dif-ferent nucleophiles afforded aziridines, thiiranes,c yclopropanes, dihydrofurans, dihydroisoxazole, dibenzyloxymethylfuran, and isonucleosides in moderate to good yields. This powerful and practical route provides an ew platform for synthetic applicationso fr enewable biomass precursors and adds to the toolbox for chemists interested in new chemical entities. Supportinginformation for this article can be found under http:// dx.doi.org/10.1002/ajoc.201600183.I tc ontains 1 Ha nd 13 CNMR spectra of all new compounds, COSYs pectra( for 18 b, 20 a, 24,a nd 27 c), NOESY spectrum(for 17 c), 1D NOE difference spectra (for 18 b, 20 a,and 24), and ORTEP diagrams (for 15 h, 17 a, 22,and 30 b).populara ldoses such as d-glucose, d-mannose, d-ribose, dxylose, etc. Ac hiral ketones ynthesized from d-fructose [9] rapidly developed into an ew class of asymmetric epoxidation catalyst forthe epoxidation of olefins ( Figure 2). [10] Fructose-derived chiral 1,3-oxazolidine-2-thiones (OZTs) are also used as chiral substrates in coupling reactions ( Figure 2). [11] 1,5-Anhydro-dfructose( 1,5-AnFru) [12] and di-d-fructose dianhydrides (DFAs) [2, 13] are important precursors for the synthesis of new carbohydrate derivatives (Figure 2).We have been designing methodsf or accessing enantiopure oxaheterocycles, [14] carbocycles, [15, 16] aza-and thia-heterocycles, [16, 17] pyrroles, [18] and 1,5-disubstituted-1,2,3-triazoles [19] from monosaccharides. In line with the utilization of sugar molecules as "chiral pools"i ns ynthetic chemistry, [20] our strategy wast ou se highlyr eactive vinyl sulfone-and vinyl sulfoxide-modified carbohydrates, [21] which are powerful Michael acceptors ande fficient partners in cycloaddition reactions. [15, 19] More recently,w eh ave introduced vinyl selenone-modified carbohydrates as efficient Michael acceptors in diversity oriented synthesis (DOS) to generate complex molecular scaffolds. [22] The aryl selenoyl functionality of vinyl selenone plays ad ual role as an efficient electron-withdrawing group as well as al eaving group, allowing Michael addition followed by elimination in tandem fashion. [22] Although vinyl selenones are widely used in simple systems [23] and nucleosides, [24] vinyl selenones derived from carbohydrates have rarely been utilized partly because of the notoriously unpredictable stability of carbohydrate selenones or selenoxides. [25,26] Nevertheless,w e have designed and used stable vinyl selenone-modified furanosides for generating new molecules. [22,26] As d-fructose is now considered as an intermediate for generating small molecules such as 2,5-dimethylfuran, 5-hydroxymethy...

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ChemInform Abstract: A General and Diastereoselective Route to Five‐Membered Carbocycles and Heterocycles from Acyclic Vinyl Sulfone‐Modified Carbohydrates.

Atta

Pathak

2010

ChemInform

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A General and Diastereoselective Route to Five‐Membered Carbocycles and Heterocycles from Acyclic Vinyl Sulfone‐Modified Carbohydrates

Cited by 10 publications

References 84 publications

Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral Pyrrolidines

Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral Pyrrolidines

Vinyl Selenones Derived from d‐Fructose: A New Platform for Fructochemistry

ChemInform Abstract: A General and Diastereoselective Route to Five‐Membered Carbocycles and Heterocycles from Acyclic Vinyl Sulfone‐Modified Carbohydrates.

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