Mercury-free preparation and selective reactions of propargyl (and propargylic) Grignard reagents.
ZnBr2 was found to catalyze formation of propargyl and propargylic Grignard reagents, and thus put an end to the standard method using a mercury catalyst. The Grignard reagents were submitted to addition reaction with carbonyl compounds and allylation with the cyclic monoacetate to afford the propargyl-type products selectively. Furthermore, the product from the monoacetate was transformed to an acetylene analogue of 2-(5,6-epoxyisoprostane A2)phosphorylcholines.
Acharya
Hukum P
HP
Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan.
Miyoshi
Kei
K
Kobayashi
Yuichi
Y
D000085:Acetates / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D008274:Magnesium / Q000737:chemistry*; D008628:Mercury; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010767:Phosphorylcholine / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
D000085:Acetates; D000480:Alkynes; D000498:Allyl Compounds; D001965:Bromides; D009019:Morphinans; C440369:N-propargyl; D009942:Organometallic Compounds; D010767:Phosphorylcholine; D008628:Mercury; D008274:Magnesium; D015032:Zinc