Stereocontrolled synthesis of novel enantiomerically pure sulfides and selenides from (+)-camphor and (+)-camphor-10-sulfonyl chloride

Procter, David J.; Archer, Nicolas J.; Needham, Robert; Bell, David; Marchington, Allan P.; Rayner, Christopher M.

doi:10.1016/s0040-4020(99)00507-4

Cited by 22 publications

(9 citation statements)

References 51 publications

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“…If chiral ketones like camphor are employed, the Lewis acid catalyzed hemiselenoacetal formation and the subsequent reduction of the selenonium ion yields enantiomerically pure selenides of type 10 (Scheme 5). [16] Me Me Other versatile reactions with selenium nucleophiles such as substitution reactions with aryl or alkyl halides, Michael reactions, or ester and lactone cleavages are not discussed herein, because these reactions have not been used in stereoselective synthesis. Also polymer-bound selenium nucleophiles have not yet been employed to perform the abovementioned reactions.…”

Section: Reviewsmentioning

confidence: 99%

Organoselenium Chemistry in Stereoselective Reactions

Wirth

2000

Angew. Chem. Int. Ed.

302

188

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Selenium‐based methods have developed rapidly over the past few years asnd organoselenium chemistry has become a very useful tool in the hands of synthetic chemists. The different reactivity of selenium‐containing compounds in contrast to the sulfur analogues has led to versatile and new synthetic methods in organic chemistry. Various functionalities can be selectively introduced into complex molecules under very mild reaction conditions. In this review, the principles of organoselenium chemistry are traced back to their origins and are highlighted with respect to stereoselective synthesis. The unique properties of selenium allow the development of new and highly selective transformations, which can be employed subsequently in new routes for the synthesis of versatile chiral building blocks and for natural product synthesis.

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Section: Reviewsmentioning

confidence: 99%

Organoselenium Chemistry in Stereoselective Reactions

Wirth

2000

Angew. Chem. Int. Ed.

302

188

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“…The reaction of aryl halides and thiols is the typical method to construct C‐S bonds . Researchers also built other important methods for the formation of thioethers, such as the addition of thiols to carbonyl compounds followed by the in‐situ reduction of the generated intermediate thionium ion, deoxygenation of sulfoxides, cross‐coupling of aryl boronic acids and alkyl thiols or N ‐thio(alkyl, aryl, heteroaryl)imides,, , metal catalyzed hydrothiolation of alkynes and so on . During the development of the system for synthesis of thioethers, significant progress has been made.…”

Section: Introductionmentioning

confidence: 99%

Efficient Thiolation of Alcohols Catalyzed by Long Chained Acid‐Functionalized Ionic Liquids under Mild Conditions

et al. 2019

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Thioethers as important building blocks have been usually found in organic synthesis. Herein, a series of long chained acid‐functionalized ionic liquids derived from pyrrolidine were applied for the thiolation of alcohols to synthesize different compounds containing thioether structures. This kind of ionic liquids exhibited higher efficiency than general ionic liquids based on imidazole, providing up to 99 % yield with [BsCtP][OTf] as the catalyst at room temperature for 0.25 h. The results indicated that the activities of the ionic liquids have relationship with the side chain length of ionic liquids based on pyrrolidine, anions and cations. The catalytic system had wide substrate scope and was applicable for the reaction of aromatic primary and secondary alcohols and thiols including aliphatic and aromatic thiols, benzothiazole‐2‐thiols and benzooxazole‐2‐thiols. Besides, there was no obvious change in activity of the catalyst after six runs. Thus, the catalytic system exhibited good recyclability. Additionally, carbocations should be the key intermediate and several functionalized groups of the ionic liquids have synergetic effect for the thiolation.

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“…32 The enantiomerically pure selenides resulting from this work are potentially useful sources of chiral selenium containing compounds. Lewis acid mediated hemiacetal formation between a camphor-derived ketone and PhSeH, with subsequent in situ reduction using triethylsilane selectively gives the exo-selenide in moderate overall yield (eq 8).…”

Section: Politechnic Of Milano Milan Italymentioning

confidence: 98%