Three-Component GaHal 3 -Promoted Reactions of Substituted Methylidenemalonates and Donor-Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones.

Autor: Denisov DA; N. D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , 47 Leninsky prosp. , 119991 Moscow , Russian Federation., Borisov DD; N. D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , 47 Leninsky prosp. , 119991 Moscow , Russian Federation., Korolev VA; N. D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , 47 Leninsky prosp. , 119991 Moscow , Russian Federation., Novikov RA; N. D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , 47 Leninsky prosp. , 119991 Moscow , Russian Federation., Tomilov YV; N. D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , 47 Leninsky prosp. , 119991 Moscow , Russian Federation.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2019 May 17; Vol. 84 (10), pp. 6174-6182. Date of Electronic Publication: 2019 Apr 30.
DOI: 10.1021/acs.joc.9b00354
Abstrakt: A new cascade three-component process for high trans,trans-diastereoselective assembly of five-membered (1-halovinyl)lactones has been developed. The process is based on reactions of substituted methylidenemalonates and cyclopropanedicarboxylates with 3-haloprop-1-ynes in the presence of GaHal 3 and involves the intermediate in situ generation of 1,2-zwitterionic gallium complexes with [Ga(L) 3 ] 3+ [GaX 4 - ] 3 composition. Chloro, bromo, and iodo derivatives can be obtained successfully. Mechanistic and stereochemical aspects of the process we developed have been studied and considered in detail.
Databáze: MEDLINE