Opening of a vinyl aziridine with p-toluenesulfonamide under TBAF catalysis: synthesis of 3,4-diamino-3,4-dideoxy-l-chiro-inositol

Paul, Bernhard J.; Hobbs, Elizabeth; Buccino, Pablo; Hudlický, Tomáš

doi:10.1016/s0040-4039(01)01298-9

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Treatment Of Cyclitol Derivatives With Nitrogen Nucleophiles1

Preparation Of Ligands1

Protection and Deprotection Of N‐ans Amines1

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Cited by 31 publications

(6 citation statements)

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“…In this context, TBAF‐catalyzed opening of N ‐tosylaziridine 40 19 (see Section 2) with p ‐toluenesulfonamide has been applied to the synthesis of diamino‐inositol derivatives78 (Scheme ), as well as to that of several N ‐ and O ‐linked diinositols by iterative opening reactions of epoxides and aziridines 16…”

Section: Treatment Of Cyclitol Derivatives With Nitrogen Nucleophilesmentioning

confidence: 99%

Recent Advances in the Chemistry of Aminocyclitols

Delgado

2008

Eur J Org Chem

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Keywords: Aminocyclitols / Cyclitols / Natural products / Synthetic methodology / Stereocontrol / Disatereoselectivity / Functional group interconversion Aminocyclitols are a group of natural products with remarkable biological activities. Over the last years, significant efforts have been made to develop synthetic methodologies directed not only towards their total synthesis but also towards the design of structural analogues with improved or novel biological properties. The aim of this review is to provide the reader with a concise update of the most relevant methods for the synthesis of aminocyclitols described in the literature.

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Section: Treatment Of Cyclitol Derivatives With Nitrogen Nucleophilesmentioning

confidence: 99%

Recent Advances in the Chemistry of Aminocyclitols

Delgado

2008

Eur J Org Chem

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“…Thus, for example ytterbium() triflate has been used for the ring opening of N-tosylaziridines with primary and secondary amines. [56] Scheme 2…”

Section: Preparation Of Ligandsmentioning

confidence: 99%

Sulfonamide Ligands from Chiral Aziridines − Application to the Titanium-Mediated Addition of Diethylzinc to Benzaldehyde

Lake

Moberg

2002

Eur. J. Org. Chem.

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“…In the current armamentarium of amine‐protecting groups,1 aryl sulfonamides occupy an ambivalent position of facile formation and ease of handling but extreme robust character, undergoing cleavage only under harsh reductive (e.g. sodium naphthalenide)1a, 2 or acidic (e.g. 48 % HBr/cat.…”

Section: Protection and Deprotection Of N‐ans Aminesmentioning

confidence: 99%

ortho‐Anisylsulfonyl as a Protecting Group for Secondary Amines: Mild Ni⁰‐Catalyzed Hydrodesulfonylation

Milburn

Snieckus

2004

Angew Chem Int Ed

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Opening of a vinyl aziridine with p-toluenesulfonamide under TBAF catalysis: synthesis of 3,4-diamino-3,4-dideoxy-l-chiro-inositol

Cited by 31 publications

References 20 publications

Recent Advances in the Chemistry of Aminocyclitols

Recent Advances in the Chemistry of Aminocyclitols

Sulfonamide Ligands from Chiral Aziridines − Application to the Titanium-Mediated Addition of Diethylzinc to Benzaldehyde

ortho‐Anisylsulfonyl as a Protecting Group for Secondary Amines: Mild Ni⁰‐Catalyzed Hydrodesulfonylation

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Opening of a vinyl aziridine with p-toluenesulfonamide under TBAF catalysis: synthesis of 3,4-diamino-3,4-dideoxy-l-chiro-inositol

Cited by 31 publications

References 20 publications

Recent Advances in the Chemistry of Aminocyclitols

Recent Advances in the Chemistry of Aminocyclitols

Sulfonamide Ligands from Chiral Aziridines − Application to the Titanium-Mediated Addition of Diethylzinc to Benzaldehyde

ortho‐Anisylsulfonyl as a Protecting Group for Secondary Amines: Mild Ni0‐Catalyzed Hydrodesulfonylation

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Product

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ortho‐Anisylsulfonyl as a Protecting Group for Secondary Amines: Mild Ni⁰‐Catalyzed Hydrodesulfonylation