Stereoselective synthesis of three-membered ring compounds via ylide routes

Dai, Li‐Xin; Hou, Xue‐Long; Zhou, Yuhan

doi:10.1351/pac199971030369

Cited by 94 publications

(13 citation statements)

References 19 publications

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“…Of the two common disconnections (Figure ), the sulfur ylide approach offers potential advantages in terms of atom efficiency and facility for stereocontrol . In addition to epoxide formation, sulfur ylides can be used to prepare a wide range of synthetically valuable compounds such as aziridines and cyclopropanes , via methylidene transfer to the appropriate π acceptors such as suitably activated imines and conjugated olefins 1 Strategic disconnections in oxirane formation. …”

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confidence: 99%

Sulfur Ylides via Decarboxylation of Carboxymethylsulfonium Betaines: A Novel and Mild Protocol for the Preparation of Oxiranes

2003

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A novel protocol for the generation of sulfur ylides is described. The overall process involves thermal decarboxylation of a carboxymethylsulfonium betaine to give a sulfur ylide that, in the presence of an aldehyde, affords the corresponding terminal oxirane. Yields were found to correlate with the electron deficiency of the aryl aldehyde. In situ generation of betaine in the presence of an aldehyde successfully afforded the desired oxirane in moderate yield, thus demonstrating the feasibility of a catalytic process. [reaction: see text]

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confidence: 99%

Sulfur Ylides via Decarboxylation of Carboxymethylsulfonium Betaines: A Novel and Mild Protocol for the Preparation of Oxiranes

2003

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“…Asymmetric transformation of imines into chiral aziridines remains less well developed than the analogous transformation of aldehydes into epoxides [49,50,51]. The reported methods can be divided into three conceptual categories involving reactions of imines with: i) a-halo enolates (aza-Darzens), ii) carbenes, or iii) ylides (Scheme 1.26).…”

Section: Asymmetric Aziridination Of Iminesmentioning

confidence: 99%

Asymmetric Synthesis of Epoxides and Aziridines from Aldehydes and Imines

Aggarwal¹,

Badine²,

Moorthie³

2006

Aziridines and Epoxides in Organic Synthesis

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Epoxides and aziridines are strained three-membered heterocycles. Their synthetic utility lies in the fact that they can be ring-opened with a broad range of nucleophiles with high or often complete stereoselectivity and regioselectivity and that 1,2-difunctional ring-opened products represent common motifs in many organic molecules of interest. As a result of their importance in synthesis, the preparation of epoxides and aziridines has been of considerable interest and many methods have been developed to date. Most use alkenes as precursors, these subsequently being oxidized. An alternative and complementary approach utilizes aldehydes and imines. Advantages with this approach are: i) that potentially hazardous oxidizing agents are not required, and ii) that both C-X and C-C bonds are formed, rather than just C-X bonds (Scheme 1.1).This review summarizes the best asymmetric methods for preparing epoxides and aziridines from aldehydes (or ketones) and imines. Asymmetric Epoxidation of Carbonyl CompoundsThere have been two general approaches to the direct asymmetric epoxidation of carbonyl-containing compounds (Scheme 1.2): ylide-mediated epoxidation for the construction of aryl and vinyl epoxides, and a-halo enolate epoxidation (Darzens reaction) for the construction of epoxy esters, acids, amides, and sulfones.

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“… 1 Sulfur ylides are among the most versatile class of structural motifs, having widespread applications ranging from classical cyclopropanation, epoxidation and aziridination to more complicated [ n + 1]-cycloadditions, domino reactions and rearrangement reactions based on transition metal catalysis, organocatalysis and photocatalysis. 2 As an efficient C–C bond-forming strategy, [2,3]-sigmatropic rearrangements of sulfur ylides have been widely explored and applied since their discovery in the late 1960s. 3,4 The transition metal carbenoid-mediated rearrangement reactions between allyl sulfides and diazo species named Doyle–Kirmse reactions are representative examples and have made impressive progress especially in to the content of catalytic and asymmetric variants in the past decade ( Scheme 1a ).…”

Section: Introductionmentioning

confidence: 99%