Tin(IV) chloride catalyzed cycloaddition reactions between 3-ethoxycyclobutanones and allylsilanes.
Formal [4 + 2] cycloaddition between various 3-ethoxycyclobutanones and allyltrialkylsilanes proceeded to give 3-ethoxy-5-[(trialkylsilyl)methyl]cyclohexan-1-ones by catalysis with tin(VI) chloride. The use of allyl-tert-butyldiphenylsilane induced 1,5-hydride transfer, which gave 2-[3-(tert-butyldiphenylsilyl)propyl]-6-methyltetrahydro-4-pyrones.
Matsuo
Jun-ichi
J
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp
Sasaki
Shun
S
Hoshikawa
Takaya
T
Ishibashi
Hiroyuki
H
D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*
D000498:Allyl Compounds; D003503:Cyclobutanes; D011753:Pyrones; D012821:Silanes; D017971:Tin Compounds; C023599:stannous chloride