α,β-Epoxy sulfoxides and sulfones. Thermal and acid catalyzed rearrangements.

Tavares, Donald F.; Estep, R. E.; Blezard, M.

doi:10.1016/s0040-4039(01)98232-2

Cited by 29 publications

(3 citation statements)

References 10 publications

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“…An alternate synthesis of α-epoxy sulfones from addition of α-halosulfone anions 36 to aldehydes and ketones proceeds by a Darzens-type intermediate 35 . An enantiopure alkaloid phase-transfer catalyst has been employed for enantioselective preparation of acyclic α-epoxy sulfones 34a with ee’s up to 81% …”

Section: Phenylsulfone a Chemical Chameleon And Nearly Ideal Function...mentioning

confidence: 99%

Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

et al. 2009

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Section: Phenylsulfone a Chemical Chameleon And Nearly Ideal Function...mentioning

confidence: 99%

Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

et al. 2009

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“…In addition, compound 61 was isolated as a single diastereoisomer. We believe that this product arises from the isomerisation of phenylsulfonyloxirane 60 to the corresponding a-phenylsulfonyl aldehyde, 94 followed by a zinc-mediated intramolecular reductive amination (Scheme 33). The stereochemical outcome is most likely due to epimerisation at the carbon atom bearing the phenylsulfonyl group to the all-equatorial isomer in the presumed precursor imine 62 (Scheme 33).…”

Section: Figurementioning

confidence: 99%

Development and Applications of Amino Acid Derived Organometallics

Rilatt¹,

Caggiano²,

Jackson³

2005

Synlett

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This Account describes the discovery and development of a family of organometallic reagents derived from naturally occurring a-amino acids that have found widespread use in the stereocontrolled synthesis of non-natural analogues of proteinogenic amino acids. The general approach that we have taken involves the conversion of the side chain of enantiomerically pure naturally occurring amino acids, such as serine, aspartic acid and glutamic acid, into the corresponding primary alkyl iodide, followed by conversion into the corresponding organozinc reagents. Subsequent palladium-or copper-catalysed reactions of these reagents allow the synthesis of a wide variety of functionalised a-, b-and g-amino acid derivatives, without loss of stereochemical integrity. Insights gained from spectroscopic and kinetic studies into the stability of functionalised organozinc reagents are included.

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“…It was envisaged that two of these could be established by ring opening of an epoxide (Scheme I). The ability to obtain two stereochemically opposite epoxides from the same precursor by using the Sharpless procedure5 6 was particularly attractive. Thus the stereochemical problem devolved to a synthesis of a chiral «-substituted piperidine, a problem that has nicely been solved by the methodology developed by Husson.7 Alkylation of the chiral oxazolidine 2 derived from glutaraldehyde and (R)-phenylglycinol with 4-iodobutanal ethylene acetal gave 3 (Scheme II).…”

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confidence: 99%