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Iron‐Catalyzed Synthesis of Allenes from 2‐Alken‐4‐ynoates and Grignard Reagents
Author(s) -
Hata Takeshi,
Iwata Satoshi,
Seto Shumpei,
Urabe Hirokazu
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100995
Subject(s) - chemistry , reagent , aryl , aldol reaction , catalysis , grignard reagent , acetone , hydrolysis , grignard reaction , organic chemistry , chloride , medicinal chemistry , aqueous solution , alkyl
Treatment of 2‐alken‐4‐ynoates with methyl‐ or aryl‐Grignard reagents and iron(II) chloride (10 mol%) afforded 5‐methyl‐ or 5‐aryl‐3,4‐alkadienoates in good yields as a single isomer after aqueous work‐up. Likewise, (2‐alken‐4‐ynoyl)oxazolidinones afforded (5‐methyl‐3,4‐alkadienoyl)oxazolidinones. The aldol‐type reaction with acetone was also possible in place of the hydrolytic work‐up.