Regioselective Ring Opening of Di-isopropylsilylenes Derived from 1,3-Diols with Alkyl Lithium Reagents.
The selective alkyl lithium-induced ring opening of 1,3-di-isopropylsilylenes is described. The reaction affords a differentially substituted 1,3-diol bearing a silane that resides at the oxygen in the more sterically demanding position. The reaction can be highly selective with a regiochemical preference up to >50:1 and likely proceeds via an alkoxy-silane intermediate. This intermediate can by trapped by methyl iodide to provide the corresponding silyl methyl ether, wherein the silane again resides at the oxygen in the more sterically demanding position.
Department of Chemistry and Biochemistry, University of Colorado Boulder , Boulder, Colorado 80309, United States.
Katelyn M
KM
Chando
Department of Chemistry and Biochemistry, University of Colorado Boulder , Boulder, Colorado 80309, United States.
Patricia A
PA
Bailey
Department of Chemistry and Biochemistry, University of Colorado Boulder , Boulder, Colorado 80309, United States.
Joseph A
JA
Abramite
Department of Chemistry and Biochemistry, University of Colorado Boulder , Boulder, Colorado 80309, United States.
Tarek
T
Sammakia
D000438:Alcohols / Q000737:chemistry*; D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D007202:Indicators and Reagents; D012821:Silanes; D008094:Lithium