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Vitreoscilla hemoglobin: a natural carbene transfer catalyst for diastereo- and enantioselective synthesis of nitrile-substituted cyclopropanes.
- Source :
- Green Chemistry; 9/7/2023, Vol. 25 Issue 17, p6853-6858, 6p
- Publication Year :
- 2023
-
Abstract
- Hemoproteins have recently emerged as attractive biocatalysts for catalyzing carbene-mediated cyclopropanation, a synthetically valuable reaction not found in nature. In this study, we present a hemoglobin-catalyzed strategy for the highly stereoselective synthesis of nitrile-substituted cyclopropanes. This method offers efficiency and environmental friendliness by utilizing an asymmetric olefin cyclopropanation reaction catalyzed by wild-type Vitreoscilla hemoglobin in the presence of in situ generated diazoacetonitrile. A diverse range of nitrile-substituted cyclopropanes could be synthesized in water with exceptional stereoselectivity, achieving up to 99.9% de and ee and high turnover numbers of up to 3232. By employing this sustainable approach, not only can various chiral nitrile-substituted cyclopropanes be efficiently obtained, but also the practical application of hemoglobin in organic synthesis can be expanded. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 14639262
- Volume :
- 25
- Issue :
- 17
- Database :
- Complementary Index
- Journal :
- Green Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 170907692
- Full Text :
- https://doi.org/10.1039/d3gc01905e