The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-Bromo-2-pentyne( cas:16400-32-1 ) is researched.Name: 1-Bromo-2-pentyne.Chen, Jiahua; Hayashi, Tamio published the article 《Asymmetric Synthesis of Alkylzincs by Rhodium-Catalyzed Enantioselective Arylative Cyclization of 1,6-Enynes with Arylzincs》 about this compound( cas:16400-32-1 ) in Angewandte Chemie, International Edition. Keywords: asym synthesis alkylzinc rhodium catalyzed enantioselective arylative cyclization enyne; asymmetric carbometalation; chiral diene ligand; enantioenriched alkylzinc; rhodium catalyst. Let’s learn more about this compound (cas:16400-32-1).
A chiral diene-rhodium complex was found to catalyze the reaction of 1,6-enynes with ArZnCl to give high yields of 2-(alkylidene)cyclopentylmethylzincs with high enantioselectivity (95-99% ee). The enantioenriched alkylzincs were readily converted in a one-pot approach into a wide variety of functionalized products by taking advantage of their unique reactivity. The catalytic cycle involves arylrhodation of alkyne, intramol. alkenylrhodation of alkene, and transmetalation of the alkyl-rhodium intermediate into alkylzinc. Thus, e.g., treatment of enyne I with 4-MeOC6H4ZnCl and ZnCl2 in presence of chiral Rh complex afforded regioisomers II/III (88%, 20/1) after DOAc quenching, consistent with alkylzinc and arylzinc intermediates.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics