Asymmetric Azidoselenenylation of Alkenes: A Key Step for the Synthesis of Enantiomerically Enriched Nitrogen‐Containing Compounds

Tiecco, Marcello; Testaferri, Lorenzo; Santi, Claudio; Tomassini, Cristina; Marini, Francesca; Bagnoli, Luana; Temperini, Andrea

doi:10.1002/ange.200351229

Cited by 66 publications

(79 citation statements)

References 22 publications

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“…10 This was then used in a CuAAC reaction to afford triazolic compounds in up to 94% ee. There has been a wide range of asymmetric methodologies developed for the formation of chiral azides and alkynes, which have been successfully used to synthesise a range of important compounds.…”

Section: Chiral Starting Materialsmentioning

confidence: 99%

Asymmetric Copper-Catalyzed Azide–Alkyne Cycloadditions

2016

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Since it's discovery independently by Sharpless and Meldal in 2002 the copper catalysed azide-alkyne cycloaddition (CuAAC) has become a ubiquitous molecular linking platform. Easy access to substituted 1,4-triazoles can be exploited to engender asymmetry to a myriad of potentially useful targets in high yields. Utilising the CuAAC to form chiral triazolic products in a single step is an attractive and powerful approach for the synthetic chemist. The area of asymmetric CuAAC is still in its infancy compared to more established asymmetric metal mediated transformations, however this leads to exciting challenges that need to be overcome to usher in the next era in the story of the triazole and click chemistry in general. This review details the steps taken into asymmetric CuAAC and the exciting results achieved thus far.

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Section: Chiral Starting Materialsmentioning

confidence: 99%

Asymmetric Copper-Catalyzed Azide–Alkyne Cycloadditions

2016

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“…Enantioselective lipase-catalyzed kinetic resolutions of com- (11))], c = ee(10)/[ee(10) + ee (11) cis-1,2-Amino alcohols can be prepared starting from antib-hydroxy selenides through displacement of the phenylselenonyl group, following the procedure developed by Tiecco. 20 For this reason, we investigated the enzymatic resolution of compound (±)-8e.…”

Section: Resultsmentioning

confidence: 99%

Lipase-catalyzed resolution of anti-6-substituted 1,3-dioxepan-5-ols

Gruttadauria

Meo

Riela

et al. 2006

Tetrahedron: Asymmetry

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Abstract-Several anti-6-substituted 1,3-dioxepan-5-ols were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30°C. This approach provided, in some cases, the alcohol and the acetate in high enantiomeric purity, depending on the nature of the substituent (R = N 3 , SePh, I, OBn) and the acetal group (unsubstituted or dimethyl). The role of the size of substituents is also discussed. Enantiopure anti-6-substituted 1,3-dioxepan-5-ols are useful building blocks.

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“…13 These two diselenides were extensively used in our laboratory. We have also employed the easily available camphor diselenide 3 which was introduced by Back.…”

Section: Syntheses and Reactions Of Organoselenium Reagentsmentioning

confidence: 99%

“…is slightly lower. 12,13,14 The two diastereoisomeric selenium containing reaction products could not be separated and the reductive deselenenylation afforded tetrahydrofurans 6 with an ee equal to the D.r. Under the same conditions the cyclofunctionalizations of alkenoic acids 7 (Selenolactonization) afforded seleno γ-lactones 8 and then the γ-lactones 9 with similarly good diastereoselectivities (Scheme 5).…”

Section: Cyclization Reactions By Formation Of Carbon Oxygen Bondsmentioning

confidence: 99%