Pentacoordinate Organosilicate-Catalyzed Michael Addition of β-Keto Esters to 3-Buten-2-one

✍ Scribed by Jun-ichi Tateiwa; Akira Hosomi

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 200 KB
• Volume: 2001
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200104)2001:8<1445::aid-ejoc1445>3.0.co;2-q

✦ Synopsis

The Michael addition of β-keto esters to 3-buten-2-one (methyl vinyl ketone, MVK) in the presence of a pentacoordinate organosilicate was investigated. Ethyl 2-oxo-1-cyclohexanecarboxylate reacted with MVK in the presence of potassium bis(1,2-benzenediolato)phenylsilicate to furnish ethyl 2-oxo-1-(3-oxo-1-butyl)-1-cyclohexanecarboxylate in 96% isolated yield. Ethyl 2-oxo-1-cyclopentanecarboxylate, ethyl Scheme 1 [ ‡] Organometallic Ate Compounds in Organic Synthesis, 38. Ϫ Part 37: Ref. [1] [a