Regioselective and enantioselective substitution of allylic sulfoximines with organocopper reagents. A versatile approach to optically active isocarbacyclins

Bund, Joerg; Gais, Hans‐Joachim; Erdelmeier, Irène

doi:10.1021/ja00004a071

Cited by 49 publications

(12 citation statements)

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“…A) The addition-elimination-isomerisation (AEI)-sequence developed by Gais et al 128,132 B) Addition of vinyl cuprates to chloromethyl sulfoximines also developed by Gais. 131 C) Nucleophilic ring opening of cyclic sulfonimidates 53 (Schemes 9 and 27, see also Section 2.3).…”

Section: Scheme 26mentioning

confidence: 99%

Sulfoximines: Structures, Properties and Synthetic Applications

2000

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This review presents a comprehensive treatment of sulfoximine chemistry particularly emphasising synthetic developments and structural work after 1985. Following a brief introduction, the structures and properties of sulfoximines and metallated sulfoximines are discussed. The second section deals with the preparation of sulfoximines emphasising new methods. The main part of the review is concerned with reactions of sulfoximines. The material in this section is organised based on the reactivity pattern displayed by the various sulfoximines. Therefore they are grouped roughly into three classes of compounds. The first group of sulfoximines comprises compounds acting as C-nucleophiles, the second one contains electrophilic sulfoximines and the last group is made up of sulfoximines being useful as (chiral) ligands particularly for transition metals. Finally the ability of sulfoximines to act as "chiral chemical chameleons" and their rôle in biological and medicinal chemistry is briefly discussed.

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Section: Scheme 26mentioning

confidence: 99%

Sulfoximines: Structures, Properties and Synthetic Applications

2000

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“…[16] When subjecting chiral allylic sulfoximines 14 to treatment with homocuprate reagents (R 2 CuLi/LiI), the conditions would favor the α-selective allylation adduct, whereas tuning of the reaction parameter with an organocopper reagent in the presence of BF 3 ·OEt 2 , would yield regio-and enantioselective exocyclic alkenes with a maximum of 90 % ee for the cyclopentenyl substrate (Scheme 6). Another set of chiral leaving groups in the form of heterocyclic moieties was first described by Caló and co-workers.…”

Section: Diastereoselective Proceduresmentioning

confidence: 99%

Copper‐Catalyzed Asymmetric Allylic Alkylation

2008

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“…In particular, allylic sulfoximines have gained much attention in this area. Amongst the successful applications of these compounds are asymmetric S N 2′‐reactions with organo cuprates2, 3 and allyl transfer reactions 4–6. The primarily formed vinyl sulfoximines of the latter reaction can be transformed to isomerically pure highly substituted tetrahydrofurans,7 oxabicyclic systems,8 and pyrrolidines 9, 10.…”

Section: Introductionmentioning

confidence: 99%

Cyclic Sulfonimidates by Dynamic Diastereomer-Differentiating Cyclisation: Large-Scale Synthesis and Mechanistic Studies

Reggelin

Junker

2001

Chem. Eur. J.

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A dynamic diastereomer differentiating cyclisation is the key step in a new large-scale synthesis of both enantiomers of the cyclic sulfonimidates 1 (Aldrich no. 54099-4) and ent-1 (Aldrich no. 54412-4). These are valuable starting materials in the asymmetric synthesis of chiral oxa- and azaheterocyclic compounds. NMR spectroscopic studies on the reacting system reveal N-chloro sulfinamides to be reactive intermediates in the oxidative chlorination of sulfinamides with tert-butyl hypochlorite and allow for the inspection of the configurational behaviour of the involved sulfonimidoyl chlorides and sulfonimidoyl bromides.

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Regioselective and enantioselective substitution of allylic sulfoximines with organocopper reagents. A versatile approach to optically active isocarbacyclins

Cited by 49 publications

References 1 publication

Sulfoximines: Structures, Properties and Synthetic Applications

Sulfoximines: Structures, Properties and Synthetic Applications

Copper‐Catalyzed Asymmetric Allylic Alkylation

Cyclic Sulfonimidates by Dynamic Diastereomer-Differentiating Cyclisation: Large-Scale Synthesis and Mechanistic Studies

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