131784-71-9Relevant articles and documents
Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition
Varlet, Thomas,Mati?i?, Mateja,Van Elslande, Elsa,Neuville, Luc,Gandon, Vincent,Masson, Géraldine
supporting information, p. 11611 - 11619 (2021/08/16)
A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.
Synthesis of indoles via 6π-electrocyclic ring closures of trienecarbamates
Greshock, Thomas J.,Funk, Raymond L.
, p. 4946 - 4947 (2007/10/03)
A new method for the preparation of indoles from readily available α-haloenones and α-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure
