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Creators/Authors contains: "Sengupta, Arkajyoti"

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  1. ; ; ; (, The Journal of Organic Chemistry)
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  2. ; ; ; ; ; ; ; (, Nature Chemistry)
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  3. ; (, The Journal of Physical Chemistry A)
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  4. ; ; ; ; ; ; (, Nature Catalysis)
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  5. ; ; ; ; (, Journal of Chemical Theory and Computation)
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  6. ; ; (, The Journal of Organic Chemistry)
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  7. ; ; ; ; (, Accounts of Chemical Research)
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  8. ; ; (, Journal of the American Chemical Society)
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  9. ; ; ; ; ; ; ; ; (, Journal of the American Chemical Society)
    Propargyl amines are versatile synthetic intermediates with numerous applications in the pharmaceutical industry. An attractive strategy for efficient preparation of these compounds is nitrene propargylic C(sp3)−H insertion. However, achieving this reaction with good chemo-, regio-, and enantioselective control has proven to be challenging. Here, we report an enzymatic platform for the enantioselective propargylic amination of alkynes using a hydroxylamine derivative as the nitrene precursor. Cytochrome P450 variant PA-G8 catalyzing this transformation was identified after eight rounds of directed evolution. A variety of 1-aryl-2-alkyl alkynes are accepted by PA G8, including those bearing heteroaromatic rings. This biocatalytic process is efficient and selective (up to 2610 total turnover number (TTN) and 96% ee) and can be performed on preparative scale. 
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  10. ; ; (, The Journal of Physical Chemistry A)
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