Insertion reactions of alkenes with diterpenoid chromium aminocarbenes |
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| Institution: | 1. Department of Inorganic Chemistry, University of Pécs and Szentágothai Research Centre, H-7624, Pécs, P.O. Box 266, Hungary;2. Department of Physical Chemistry, University of Debrecen, H-4032, Debrecen, Egyetem tér 1, Hungary;3. MTA-PTE Research Group for Selective Chemical Syntheses, H-7624, Pécs, Ifjúság u. 6, Hungary;1. Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France;2. Institute for Integrative Biology of the Cell (I2BC), CNRS, CEA, Univ. Paris-Sud, Université Paris-Saclay, 91191 Gif-sur-Yvette Cedex, France;3. Aix Marseille Univ, CNRS, IM2NP, Marseille, France;4. Aix Marseille Univ, CNRS, BIP, Marseille, France |
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| Abstract: | Insertion reactions of electron-deficient alkenes with chromium aminocarbenes derived from podocarpic acid generally give aryl ketone products derived from ring opening of an aminocyclopropane and subsequent enamine hydrolysis, the exception being alkenyl sulphones which give products derived from insertion of the carbene into the β-CH bond of the alkene. Increasing steric hindrance due to the substituents on the aminocarbene nitrogen appears to result in higher yields of the insertion products. However, other factors such as stabilisation of the intermediate tetracarbonylaminocarbene may explain why morpholinocarbenes give superior yields of the insertion products. Propenoic acid, propenal or nitropropene give a 13-formyl-substituted diterpenoid. Electron-rich alkenes do not undergo insertion reactions with these aminocarbenes at 110°C. |
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