l-Isoleucine derived bifunctional phosphine catalyses asymmetric [3 + 2]-annulation of allenyl-esters and -ketones with ketimines

Autor:	Carsten Strohmann, Kamal Kumar, Miguel Garcia‐Castro, Muthukumar G. Sankar, Christopher Golz
Rok vydání:	2016
Předmět:	Annulation Natural product 010405 organic chemistry General Chemical Engineering Isatin L-Isoleucine General Chemistry 010402 general chemistry 01 natural sciences Small molecule 0104 chemical sciences chemistry.chemical_compound chemistry Organic chemistry Bifunctional Phosphine
Zdroj:	RSC Advances. 6:56537-56543
ISSN:	2046-2069
DOI:	10.1039/c6ra12387b
Popis:	The zwitterionic 1,3-dipoles generated by the addition of a bifunctional L-isoleucine derived N-acylaminophosphine to allenic esters as well as ketones were successfully trapped with isatin derived ketimines in a [3 + 2]-annulation reaction to deliver 3,2′-dihydropyrrolyl spirooxindoles in high yields (up to 88%) and with excellent enantioselectivities (up to >99%). The asymmetric annulation reaction provides a facile access to biologically relevant small molecules embodying the natural product spirocyclic core.
Databáze:	OpenAIRE
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