Use of hindered silyl ethers as protecting groups for the non-aldol aldol process.
[reaction: see text] Bulky epoxy bis-silyl ethers, e.g., 15, derived from 5-trialkylsilyloxy-2-alken-1-ols by epoxidation and silylation were treated with TMSOTf to afford non-aldol aldol rearrangement products, the 3,5-bis(silyloxy)alkanals, e.g., 16, with little to none of the corresponding tetrahydrofurans.
Jung
Michael E
ME
Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
Hoffmann
Barbara
B
Rausch
Bernhard
B
Contreras
Jean-Marie
JM
D000447:Aldehydes / Q000138:chemical synthesis; D004987:Ethers / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D011422:Propionates / Q000138:chemical synthesis*
D000447:Aldehydes; D004987:Ethers; D017646:Organosilicon Compounds; D011422:Propionates