Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes.
Two consecutive ruthenium-catalyzed reactions have been achieved for the synthesis of siloxacycles from terminal alkenyl carbenols and alkynylsilanes. The metal-catalyzed dehydrogenative condensation between alcohols and silanes, generating molecular hydrogen as the only byproduct, allows for the subsequent enyne metathesis without isolating the intermediate silyl ethers. This system provides a streamlined synthesis of synthetically useful building blocks. [reaction: see text]
Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
Reagan L
RL
Miller
Sarah V
SV
Maifeld
Daesung
D
Lee
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry; D012833:Siloxanes / Q000737:chemistry*
D000438:Alcohols; D000475:Alkenes; D000480:Alkynes; D004987:Ethers; D012821:Silanes; D012833:Siloxanes; D012428:Ruthenium