Intramolecular [1,4]-S- to O-silyl migration: a useful strategy for synthesizing Z-silyl enol ethers with diverse thioether linkages.
An intramolecular [1,4]-S- to O-silyl migration has been used to form silyl enol ethers with Z-configurational control. The silyl migration also creates a new anion center at sulfur, which can subsequently react with electrophiles to generate Z-silyl enol ethers with diverse thioether linkages. The synthetic utility of this pathway was demonstrated by modifying the Z-silyl enol ethers with aldehydes via a Mukaiyama aldol reaction or Prins cyclization to generate functionalized organosulfur compounds.
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
Changzhen
C
Sun
Yuebao
Y
Zhang
Peihong
P
Xiao
Hongze
H
Li
Xianwei
X
Sun
Zhenlei
Z
Song
D000838:Anions / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
D000838:Anions; D012821:Silanes; D013440:Sulfides; D013455:Sulfur