Dual function catalysts. Dehydrogenation and asymmetric intramolecular Diels-Alder cycloaddition of N-hydroxy formate esters and hydroxamic acids: evidence for a ruthenium-acylnitroso intermediate.
The chiral ruthenium salen complex, 13b, functions as an efficient catalyst for the sequential oxidation and asymmetric Diels-Alder cycloaddition of hydroxamic acids and N-hydroxy formate esters. This result provides evidence for the formation of a ruthenium-nitroso formate (acyl nitroso) intermediate. The Diels-Alder precursors are prepared from simple building blocks, and the cycloadducts, bridged oxazinolactams, can serve as useful intermediates in organic synthesis.
Chow
Chun P
CP
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Shea
Kenneth J
KJ
D002384:Catalysis; D003500:Cyclization; D005561:Formates / Q000737:chemistry*; D006865:Hydrogenation; D006877:Hydroxamic Acids / Q000737:chemistry*; D006880:Hydroxy Acids / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D009603:Nitroso Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D005561:Formates; D006877:Hydroxamic Acids; D006880:Hydroxy Acids; D007769:Lactams; D009603:Nitroso Compounds; D009942:Organometallic Compounds; D010078:Oxazines; D012428:Ruthenium