Preparation of oxetanes by silicon-directed 4-exo trig electrophilic cyclisations of homoallylic alcohols

Rofoo, Mazin; Roux, Marie-Claude; Rousseau, G.

doi:10.1016/s0040-4039(01)00227-1

Cited by 25 publications

(9 citation statements)

References 20 publications

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“…Rousseau et al reported the exo-bromocycloetherification of E-silylhomoallylic alcohol 103 and its Z-isomer 103' using bis(sym-collidine)bromine(I) hexafluoroantimonate (Br + (Coll)2SbF6 -) [106]. In the related 4-exo cyclization reaction there was the problem of the competing 5-endo cyclization, while the introduction of a silyl group to the olefinic moiety contributed toward the high selectivity of the reaction.…”

Section: Enantioselective Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties via the generation of halonium intermediates, followed by the attack of carbon-, nitrogen-, oxygen-, and sulfur-containing nucleophiles to give highly functionalized carbo- and heterocycles. Interestingly, new transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products according to the difference in the size and number of halogen atoms have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

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Section: Enantioselective Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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“…It is developed by the same group that developed silicon-directed 4-exo-rig electrophilic cyclizations of homoallylic alcohols to prepare oxetanes (Scheme 106). 113 Shi and coworkers reported that various g-hydroxyalkenes and g-amino-alkenes could efficiently undergo bromocyclization using NBS as the Br þ source with chiral phosphoric acid 401 as the catalyst, giving 2-substituted THFs and tetrahydropyrroles with generally good yields and up to 91% ee (Scheme 107). 114 Fujioka and coworkers reported an example of asymmetric bromolactonization of 5-substituted 5-hexenoic acids catalyzed by a C3-symmetric chiral trisimidazoline (Scheme 108).…”

Section: Cyclization Involving Alkenesmentioning

confidence: 99%

4.07 Electrophilic Cyclization

Jiang

Liu

2014

Comprehensive Organic Synthesis II

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“…Few methodological studies have been done. Rousseau et al have published the preparation of oxetanes via a 4-endo cyclization process on allylic alcohols [169,170] and via a 4-exo cyclization process on homoallylic alcohols [171], using the electrophilic reagent bis(sym-collidine)bromine(I) hexafluorophosphate (HBB) or hexafluoroantimonate. This reaction was also used to prepare b-lactones starting from a,b-unsaturated acids (Scheme 3.88) [169].…”

Section: Electrophilic Cyclizationsmentioning

confidence: 99%