Abstract
The photochemical reaction of chromium carbene complexes with imines has been developed into an efficient process for the synthesis of (β-lactams. A new route to aminocarbene complexes, involving the reaction of Na2Cr(CO)5 with amides and trimethylsilyl chloride has been developed. Using this procedure, chiral, optically active aminocarbene complexes have been prepared, and their photochemical reactions with imines developed. Chiral, optically active (β-lactams have been prepared with >90% diastereoselectivity by this procedure.
A mechanistic study of the photochemical β-lactam-forming reaction implicated metal-bound ketenes as key intermediates. Chiral aminocarbene complexes having a pendant OH group were synthesized. Photolysis of these resulted in the production of chiral aminolactones which could be cleaved to chiral amino acids.
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© 1989 Kluwer Academic Publishers
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Hegedus, L.S. (1989). Photolytic Reactions of Chromium Carbene Complexes in the Synthesis of Optically Active, Biologically Active Compounds. In: Schubert, U. (eds) Advances in Metal Carbene Chemistry. NATO ASI Series, vol 269. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-2317-1_27
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DOI: https://doi.org/10.1007/978-94-009-2317-1_27
Publisher Name: Springer, Dordrecht
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