A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.
A convenient Grubbs II metathesis provides dihydrooxasilines by relay RCM (RRCM). Dihydrooxasilines undergo ring opening to give Z-vinyl silanes. These can then be converted to Z-vinyl iodides. This sequence provides a short, high yield, and convenient route to trisubstituted Z-vinyl iodides, useful intermediates for the preparation of polypropionate antibiotics.
Xie
Qiuzhe
Q
Department of Chemistry, SUNY Stony Brook, Stony Brook, New York 11794-3400, USA.
Denton
Richard W
RW
Parker
Kathlyn A
KA
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007455:Iodine / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D012821:Silanes; D007455:Iodine