C-2/c-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.
The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.
Bajtos
Barbora
B
Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 1Y2, Canada.
Yu
Ming
M
Zhao
Hongda
H
Pagenkopf
Brian L
BL
D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D000577:Amides / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000577:Amides; D003521:Cyclopropanes; D004952:Esters; D007211:Indoles; C059688:alkoxyl radical; D002244:Carbon; C030797:cyclopropane