Stereoselective additions of chiral (E)-crotylsilanes to thionium ions: asymmetric synthesis of homoallylic thioethers.
Stereochemically well-defined homoallylic thioethers 3 are synthesized via Lewis acid promoted condensation reaction between chiral organosilane reagents 2 and in situ generated thionium ions. The stereochemical course of the reaction is consistent with earlier reports concerning crotylsilations of oxonium ions.
Liu
Ping
P
Department of Chemistry and Center for Streamline Synthesis, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Binnun
Eva D
ED
Schaus
Jennifer V
JV
Valentino
Nicole M
NM
Panek
James S
JS
D000080:Acetals / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry; D000440:Butanols / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry; D017971:Tin Compounds / Q000737:chemistry
D000080:Acetals; D000473:Alkanes; D000440:Butanols; D004987:Ethers; D007659:Ketones; D000644:Quaternary Ammonium Compounds; D012821:Silanes; D017971:Tin Compounds; C041694:stannic chloride; D013455:Sulfur; C059915:thionium