Efforts toward distorted spiropentanes.
Kuan-Jen Su, Jean-Luc Mieusset, Vladimir B Arion, Wolfgang Knoll, Lothar Brecker, Udo H Brinker
Index: J. Org. Chem. 21th ed., 75 , 7494-7497, (2010)
Full Text: HTML
Abstract
Tetravinylbenzene 4 was prepared in nearly quantitative yield from commercially available tetrabromobenzene; the improved, one-step procedure now employs Suzuki-Miyaura cross-coupling conditions. Intermolecular cyclopropanation of 4 with dibromocarbene gave a series of gem-dibromide adducts. Intramolecular cyclopropanation of monoadduct 5, putatively by its methyllithium-generated cyclopropylidene(oid), produced compound 11, which features a highly distorted spiropentane having a C-C-C bond angle of 163.5°. The stability of the reported spiropentanes was investigated using DFT calculations.
Related Compounds
Related Articles:
Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines.
2005-03-17
[Org. Lett. 6th ed., 7 , 1161-1164, (2005)]
2008-01-01
[Chemistry 3rd ed., 14 , 886-894, (2008)]
2010-01-01
[Bioorg. Med. Chem. 8th ed., 18 , 2894-2901, (2010)]
Kinetic resolution of axially chiral 2,2'-dihydroxy-1,1'-biaryls by palladium-catalyzed alcoholysis.
2005-08-03
[J. Am. Chem. Soc. 30th ed., 127 , 10474-10475, (2005)]
Structure based design, synthesis and SAR of cyclic hydroxyethylamine (HEA) BACE-1 inhibitors.
2011-04-01
[Bioorg. Med. Chem. Lett. 7th ed., 21 , 1942-1947, (2011)]