The first diastereoselective nitroaziridination of N-tosylaldimines with 1-bromonitroalkanes

Yadav, Lal Dhar S.; Garima, .; Kapoor, Ritu

doi:10.1016/j.tetlet.2009.07.054

Cited by 14 publications

(3 citation statements)

References 67 publications

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“…MeOH/NaOAc was found to be the best solvent/base system for this procedure, furnishing aziridines 186 in good yields and with cis-selectivity (Scheme 79). 108 An asymmetric version of the aza-Darzens aziridination could be realized by using a chiral auxiliary that could be part of either the imine or the anionic component. Concerning the use of chiral imines, chiral sulfinimines have been shown to be suitable substrates for this scope.…”

Section: Aza-darzens Reactionmentioning

confidence: 99%

“…In a recent paper, Yadav and co-workers reported the first example of diastereoselective nitroaziridination of N -tosylaldimines 184 with 1-bromonitroalkanes 185 . MeOH/NaOAc was found to be the best solvent/base system for this procedure, furnishing aziridines 186 in good yields and with cis-selectivity (Scheme ) …”

Section: Stereoselective Aziridination By Transfer Of Carbon To Iminesmentioning

confidence: 99%

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Recent Advances in the Stereoselective Synthesis of Aziridines

2014

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Section: Aza-darzens Reactionmentioning

confidence: 99%

Section: Stereoselective Aziridination By Transfer Of Carbon To Iminesmentioning

confidence: 99%

Recent Advances in the Stereoselective Synthesis of Aziridines

2014

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“…The reactions between N ‐tosylaldimines 9 , 1‐bromonitroalkanes 3 and NaOAc thus afford 2‐nitro‐1‐tosylaziridines 36 in 78–92 % yields with 81–98 % Z diastereoselectivity in a one‐pot procedure (Table 17). 37…”

Section: Gem‐halonitroalkanesmentioning

confidence: 99%

Recent Developments in the Chemistry of gem‐Halonitro Compounds

2014

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gem‐Halonitro compounds are valuable synthetic intermediates of growing chemical interest that have been known for many years. Initially, the interest in gem‐halonitro compounds lay in their biological activity, whereas their chemistry remained quite underdeveloped. In the past few years, however, interest in the chemistry of gem‐halonitro compounds has grown exponentially, sparked by some recent investigations into the reactivity of the gem‐halonitro moiety. Nowadays, gem‐halonitro compounds are recognized as powerful chemical tools on account of their usefulness as synthetic intermediates. This review highlights recent synthetic strategies based on gem‐halonitro compounds and provides an overview of their usefulness in organic chemistry.

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Bromonitromethane

Inokuma¹,

Takemoto²

2010

Encyclopedia of Reagents for Organic Synthesis

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The first diastereoselective nitroaziridination of N-tosylaldimines with 1-bromonitroalkanes

Cited by 14 publications

References 67 publications

Recent Advances in the Stereoselective Synthesis of Aziridines

Recent Advances in the Stereoselective Synthesis of Aziridines

Recent Developments in the Chemistry of gem‐Halonitro Compounds

Bromonitromethane

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