How the Binding of Substrates to a Chiral Polyborate Counterion Governs Diastereoselection in an Aziridination Reaction: H-Bonds in Equipoise

Vetticatt, Mathew J.; Desai, Aman A.; Wulff, William D.

doi:10.1021/ja103863j

Cited by 53 publications

(69 citation statements)

References 24 publications

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“…30 Thus, the presence or absence of an amidic proton plays an important role in diastereoselection. The …”

Section: Scheme 10mentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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The inherent reactivity of the aziridine ring due to ring-strain makes it valuable building blocks for the synthesis of other heterocyclic motifs of biological relevance. Of particular significance is the generation of azomethine ylides from them and cycloaddition of ylides with alkenes, alkynes, and heterocumulenes. The ring undergoes opening followed by cyclization with a variety of reagents either in the presence of a catalyst or without any catalyst. This review article discusses the recent applications of aziridines in syntheses of four-to seven-membered heterocycles of biological relevance such as azetidines, 2

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“…30 Thus, the presence or absence of an amidic proton plays an important role in diastereoselection. The …”

Section: Scheme 10mentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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“…1–4 This AZ reaction is highly enantioselective and diastereoselective giving either cis - 1,2 or trans -aziridines 2,3 with a variety of imines and diazo compounds. Shortcomings of the optimized protocol include the need to generate a pre-catalyst from the VAPOL or VANOL ligand and B(OPh) 3 and the need to prepare an imine from an aldehyde and an amine.…”

Section: Introductionmentioning

confidence: 99%

BOROX Catalysis: Self-assembled amino-BOROX and imino-BOROX Chiral Brønsted Acids in a Five Component Catalyst Assembly/Catalytic Asymmetric Aziridination

Gupta

Mukherjee

et al. 2012

J. Org. Chem.

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A five-component catalyst assembly/aziridination reaction is described starting from an aldehyde, an amine, ethyl diazoacetate, B(OPh)3 and a molecule of a vaulted biaryl ligand (VAPOL or VANOL). A remarkable level of chemo-selectivity was observed since while 10 different products could have resulted from various reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only two other products could be detected in 3% yield. Studies reveal that the first in a sequence of three reactions is an exceedingly rapid amine induced assembly of an amino-boroxinate (AMINO-BOROX) species from VAPOL and B(OPh)3 which is followed by imine formation from the amine and aldehyde and the concomitant formation of an IMINO-BOROX species, and finally the reaction of the imine with ethyl diazoacetate mediated by the IMINO-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity.

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“…7 The successful catalyst system results from the incorporation of a molecule of benzoic acid into the VANOL boroxinate catalyst 6 . 7,8 …”

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confidence: 99%

Total Synthesis of Sedum Alkaloids via Catalyst Controlled aza-Cope Rearrangement and Hydroformylation with Formaldehyde

Ren

Wulff

2012

Org. Lett.

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The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.

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How the Binding of Substrates to a Chiral Polyborate Counterion Governs Diastereoselection in an Aziridination Reaction: H-Bonds in Equipoise

Cited by 53 publications

References 24 publications

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

BOROX Catalysis: Self-assembled amino-BOROX and imino-BOROX Chiral Brønsted Acids in a Five Component Catalyst Assembly/Catalytic Asymmetric Aziridination

Total Synthesis of Sedum Alkaloids via Catalyst Controlled aza-Cope Rearrangement and Hydroformylation with Formaldehyde

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