Synthesis and Applications of <i>tert</i>-Butanesulfinamide

Robak, MaryAnn T.; Herbage, Melissa A.; Ellman, Jonathan A.

doi:10.1021/cr900382t

Cited by 1,024 publications

(640 citation statements)

References 423 publications

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“…It should be mentioned that the N-tert-butylsulfinyl group can serve not only as an efficient chiral auxiliary, but also as an amine protecting group. 20 It could be readily cleaved under mild acidic conditions. After deprotection, the trifluoromethylated free amines 4 can be easily obtained in high yield (Scheme 3).…”

Section: Cluster Syn Lettmentioning

confidence: 99%

Regio- and Diastereoselective Vinylogous Mannich Addition of 3-Alkenyl-2-oxindoles to α-Fluoroalkyl Aldimines

Liu

Yang

Huang

et al. 2014

Synlett

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Section: Cluster Syn Lettmentioning

confidence: 99%

Regio- and Diastereoselective Vinylogous Mannich Addition of 3-Alkenyl-2-oxindoles to α-Fluoroalkyl Aldimines

Liu

Yang

Huang

et al. 2014

Synlett

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“…9a, 13 In addition, the tert-butanesulfinyl group can be cleaved using mildly acidic conditions. Furthermore, it was envisioned that the electronwithdrawing nature of the sulfinamide product would disfavor the dienone-phenol rearrangement.…”

Section: Synthesis Planmentioning

confidence: 99%

Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone

2011

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The preparation and synthetic applications of benzoquinone monoketal-derived N-tert-butanesulfinyl imines is described. These synthetically versatile intermediates undergo highly diastereoselective 1,2-addition reactions with organometallic reagents to provide 4-aminocyclohexadienones in good yields. The utility of this methodology is demonstrated in a six-step enantioselective synthesis of (-)-3-demethoxyerythratidinone.

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“…Their practicality is conferred by the electron-withdrawing nature of the chiral sulfinyl group that is also able to dictate the stereochemical outcome of transformations, such as the asymmetric synthesis of α-branched amines, allylic, homoallylic and propargylic amines, tertiary carbinamates, highly substituted aminoacids, 1,2 aminoalcohols, 1,2 and 1,3 diamines, and aziridines among others. 2 Herein we report a surprising thermal degradation of sulfinimines, which may have implications for those working with certain types of sulfinimine, for example in pharmaceutical manufacture.…”

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confidence: 91%

Isolation of stable non cyclic 1,2-disulfoxides. Revisiting the thermolysis of S-aryl sulfinimines

2014

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. (2014) Isolation of stable non cyclic 1,2-disulfoxides: revisiting the thermolysis of S-aryl sulfinimines. Chemical Communications, 50 (84). pp. 12630-12632. ISSN 1364-548XAccess from the University of Nottingham repository: http://eprints.nottingham.ac.uk/46644/1/c4cc05751a.pdf Copyright and reuse:The Nottingham ePrints service makes this work by researchers of the University of Nottingham available open access under the following conditions. This article is made available under the University of Nottingham End User licence and may be reused according to the conditions of the licence. For more details see: http://eprints.nottingham.ac.uk/end_user_agreement.pdf A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription.For more information, please contact eprints@nottingham.ac.uk DOI: 10.1039/C4CC05751A (Communication) Chem. Commun., 2014, 50, 12630-12632 Isolation of stable non cyclic 1,2-disulfoxides. Revisiting the thermolysis of S-aryl sulfinimines † ‡ José A. Souto * ab , Willian Lewis § a and Robert A. Stockman * a a School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK. Email: robert.stockman@nottingham.ac.uk; Fax: +44 (0) First published on 1st September 2014The thermolysis of S-aryl sulfinimines is shown to generate 1,2-disulfoxides and disulfides via initial Cope elimination, dimerisation of the produced sulfenic acid to a thiosulfinate, and subsequent disproportionation of the thiosulfinate.The nitrogen-carbon double bond (imine group) is a versatile moiety in synthetic organic chemistry, which is able to act as an electrophile, nucleophile or in concerted cycloadditions. Chiral sulfinimines have come to the fore as one of the most useful imine derivatives. Introduced over 20 years ago, 1 they have found extensive use both in academia and industry. Their practicality is conferred by the electron-withdrawing nature of the chiral sulfinyl group that is also able to dictate the stereochemical outcome of transformations, such as the asymmetric synthesis of α-branched amines, allylic, homoallylic and propargylic amines, tertiary carbinamates, highly substituted aminoacids, 1,2 aminoalcohols, 1,2 and 1,3 diamines, and aziridines among others. 2 Herein we report a surprising thermal degradation of sulfinimines, which may have implications for those working with certain types of sulfinimine, for example in pharmaceutical manufacture.As part of a study to extend the scope of reactivity of sulfinimine derivatives, and due to our on-going interest in the synthesis of heterocycles, 3 we started an investigation into the hetero Diels-Alder reaction 4 between crotonsulfinimine 1aa and an equimolar amount of ethyl vinyl ether as dienophile. Our attempts to perform the desired transformation were unsuccessful; however, two unexpe...

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Synthesis and Applications of tert-Butanesulfinamide

Cited by 1,024 publications

References 423 publications

Regio- and Diastereoselective Vinylogous Mannich Addition of 3-Alkenyl-2-oxindoles to α-Fluoroalkyl Aldimines

Regio- and Diastereoselective Vinylogous Mannich Addition of 3-Alkenyl-2-oxindoles to α-Fluoroalkyl Aldimines

Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone

Isolation of stable non cyclic 1,2-disulfoxides. Revisiting the thermolysis of S-aryl sulfinimines

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