| Autor: |
Dar'in D; Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504 Russia., Kantin G; Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504 Russia., Glushakova D; Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504 Russia., Sharoyko V; Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504 Russia.; The Pavlov First Medical University, 6-8 Lva Tolstogo ulitsa, Saint Petersburg 197022, Russia., Krasavin M; Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504 Russia.; Immanuel Kant Baltic Federal University, 14 Aleksandra Nevskogo ulitsa, Kaliningrad 236041, Russia. |
| Abstrakt: |
3-Diazotetramic acids were found to be valid substrates for the recently discovered approach toward natural-like Δ α,β -spirobutenolides via Rh(II)-catalyzed O-H insertion into propiolic acids followed by base-promoted intramolecular Michael addition. The target Δ α,β -spirobutenolides were obtained in generally high yields and, in the case of chiral 5-monosubstituted 3-diazotetramic acids, high diastereoselectivity. The synthesis of Δ α,β -spirobutenolides that we report here was virtually insensitive to the structure of the propiolic acids though it was somewhat sensitive to the structure of the 3-diazotetramic acids, thereby demonstrating quite a large scope. Thus, a new class of α-diazocarbonyl compounds suitable for the realization of the approach outlined above was identified. |
