Mechanism of acylation of lithium phenylacetylide with a Weinreb amide.
Additions of lithium phenylacetylide to a Weinreb amide are described. Dimeric lithium acetylide reacts via a monosolvated monomer-based transition structure. The robust tetrahedral intermediate forms sequentially a C(1) 2:2 mixed tetramer with the excess lithium acetylide and a 1:3 (alkoxide-rich) mixed tetramer. The stabilities of the mixed tetramers are consistent with a pronounced autoinhibition.
Qu
Bo
B
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853-1301, USA.
Collum
David B
DB
D000215:Acylation; D000577:Amides / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D018020:Lithium Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds; D013055:Spectrophotometry, Infrared
D000577:Amides; D018020:Lithium Compounds; D009942:Organometallic Compounds; C520500:lithium phenylacetylide