Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes.
(-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.
Bourque
Laura E
LE
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Haile
Pamela A
PA
Woerpel
K A
KA
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D000081005:Cyclohexane Monoterpenes; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008956:Models, Chemical; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry
D000498:Allyl Compounds; D000081005:Cyclohexane Monoterpenes; D003517:Cyclopentanes; D004987:Ethers; D012821:Silanes; D013729:Terpenes; C030011:carbene; C409816:isopulegol; D008697:Methane; D012825:Silicon
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