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Sulfoximines, synthesis

The chemistry of imidosulfinates is vastly unexplored [10] and nothing is known to date about the behavior of 0-allyl imidosulfinates in particular. By comparison with the known process C (Chart 1), the sulfinate-sulfone rearrangement (Sect. 2.2), it seems rather promising to try a new sulfoximine synthesis based on that rearrangement. [Pg.7]

The cyclic sulfoximine 93a,b, a key intermediate in the synthesis of sulfoximine 94 designed as inhibitors of Escherichia Coli y-glutamyl synthetase, was synthesized stereoselectively (96BMC(6)1437, 98BMC(6)1935). X-ray analysis (99AX(C55)1598) of 93b was performed, elucidating the configuration. [Pg.82]

Racemic 5-methyl-5 -(sodiomethyl)-A-(4-methylphenylsulfonyl)sulfoximine reacts with ketones to give an initial methylene transfer which produces an intermediate epoxide that is ring expanded to the oxctanc56. Application to 4-rerf-butylcyclohexanonc affords a single oxetane in 69% yield. While only achiral alkylidcne transfer reagents were utilized, in principle this reaction is amenable to the asymmetric synthesis of oxetanes. [Pg.663]

Bolm et al. [106] have carefully studied the synthesis and the hganding ability of salen-like bis(sulfoximines). The chirahty which is indeed generally introduced via the use of chiral diamines in the salen series, is in sulfoximines present via the sulfur atom. They investigated the Diels-Alder cycloaddition between cyclopentadiene and acryloyl-2-oxazolidinones with various bis(sulfoximines) (see Scheme 42) and Cu(OTf)2 as the copper source [107]. [Pg.126]

Sulfoximines bearing a chiral sulfur atom have recently emerged as valuable ligands for metal-catalysed asymmetric synthesis.In particular, C2-symmetric bis(sulfoximines), such as those depicted in Scheme 1.51, were applied to the test reaction, achieving enantioselectivities of up to 93% ee. The most selective ligand (R = c-Pent, R = Ph) of the series was also applied to the nucleophilic substitution reaction of l,3-diphenyl-2-propenyl acetate with substituted malonates, such as acetamido-derived diethylmalonate, which provided the corresponding product in 89% yield and 98% ee. [Pg.42]

In order to prepare a new range of ligands incorporating both sulfoximine and phosphine moieties, Tye et al. reported, in 2001, the synthesis of a novel chiral phosphine-sulfoximine, which was tested as a ligand in the copper-catalysed 1,4-addition of ZnEt2 to enones. Whilst the reaction of acyclic enones gave the corresponding racemic 1,4-products, the best result was obtained upon... [Pg.91]

The Harmata group s initial report concerned a one-pot, one-operation procedure <99AG(E)2419> for the synthesis of enantiomerically pure 2,1-benzothiazines via the Buchwald-Hartwig reaction reported by Bolm <98TL5731 OOJOC169> for sulfoximine N-arylation. For example, treatment of ortho-bromobenzaldehyde 78 with enantiomerically pure N-H sulfoximine 77a in the presence of a palladium catalyst and base afforded the benzothiazine 79 in 78% yield (Scheme 22). Both C-N bond formation and condensation occurred during the reaction, a phenomenon that appears general for aldehydes like 78. [Pg.15]

Reggelin et al. reported the application of methylated, enantiomerically pure acyclic and cyclic 2-alkenyl sulfoximines 203 for the synthesis of highly substituted aza(poly)cyclic ring systems 204 under complete stereocontrol <06JA4023 06S2224>. [Pg.342]

Gais and co-workers recently reported the preparation and use of chiral sulfoximine-substituted allyltitanium(iv) complexes of type 78 for the asymmetric synthesis of 3-substituted unsaturated proline derivatives 79 (Scheme 31).108... [Pg.419]

A model which rationalizes the sense of asymmetric induction has been proposed73. The alkenyl-sulfoximines 4 and 6 are useful intermediates in the synthesis of biologically active carbacyclins and isocarbacyclins 75- 77,78. [Pg.616]

We have developed asymmetric syntheses of isocarbacyclin [3] (Scheme 1.3.2) and cicaprost [4] (Scheme 1.3.3) featuring a Cu-mediated allylic alkylation of an allyl sulfoximine [5-7] and a Ni-catalyzed cross-coupling reaction of a vinyl sulf-oximine [8-10], respectively, transformations that were both developed in our laboratories. The facile synthesis of an allyl sulfoximine by the addition-elimination-isomerization route aroused interest in the synthesis of sulfonimidoyl-sub-stituted aiiyititanium complexes of types 1 and 2 (Fig. 1.3.2) and their application as chiral heteroatom-substituted allyl transfer reagents [11]. [Pg.75]

Scheme 1.3.2 Asymmetric synthesis of isocarbacyclin by the vinyl-allyl sulfoximine route. Scheme 1.3.2 Asymmetric synthesis of isocarbacyclin by the vinyl-allyl sulfoximine route.
Scheme 1.3.3 Asymmetric synthesis of cicaprost by the vinyl sulfoximine route. Scheme 1.3.3 Asymmetric synthesis of cicaprost by the vinyl sulfoximine route.
The enantiopure acyclic and cyclic allyl sulfoximines 13 and 14, respectively, required for the synthesis of the corresponding titanium complexes 1 and 2, are available from sulfoximine 12 [13] and the corresponding aldehydes and cycloal-kanones by the addition-elimination-isomerization route, which can be carried... [Pg.79]

Scheme 1.3.4 Synthesis of acyclic and cyclic allyl sulfoximines by the addition-elimination-isomerization route. Scheme 1.3.4 Synthesis of acyclic and cyclic allyl sulfoximines by the addition-elimination-isomerization route.

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Alkyl sulfoximines synthesis

Allylic sulfoximines synthesis

Asymmetric synthesis, sulfoximines

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Methionine sulfoximine, inhibition glutamine synthesis

Sulfoximine

Sulfoximines

Synthesis from sulfoximines

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