| Autor: |
Chudasama V; Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ, UK. VPEnterprise@ucl.ac.uk., Akhbar AR, Bahou KA, Fitzmaurice RJ, Caddick S |
| Jazyk: |
angličtina |
| Zdroj: |
Organic & biomolecular chemistry [Org Biomol Chem] 2013 Nov 14; Vol. 11 (42), pp. 7301-17. |
| DOI: |
10.1039/c3ob41632a |
| Abstrakt: |
In this report, a thorough evaluation of the use of aerobically initiated, metal-free hydroacylation of various C=C and N=N acceptor molecules with a wide range of aldehydes is presented. The aerobic-activation conditions that have been developed are in sharp contrast to previous conditions for hydroacylation, which tend to use transition metals, peroxides that require thermal or photochemical degradation, or N-heterocyclic carbenes. The mildness of the conditions enables a number of reactions involving sensitive reaction partners and, perhaps most significantly, allows for α-functionalised chiral aldehydes to undergo radical-based hydroacylation with complete retention of optical purity. We also demonstrate how the resulting hydroacylation products can be transformed into other useful intermediates, such as γ-keto-sulfonamides, sultams, sultones, cyclic N-sulfonyl imines and amides. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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