Catalytic asymmetric synthesis of 2,2-disubstituted oxetanes from ketones by using a one-pot sequential addition of sulfur ylide.
Better the second time around: The title compounds were synthesized by using a one-pot double methylene transfer catalyzed by a heterobimetallic La/Li complex. Chiral amplification in the second step was the key to obtaining oxetanes in high enantiomeric excess (see scheme).
Sone
Toshihiko
T
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Lu
Gang
G
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D002384:Catalysis; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008674:Metals, Rare Earth / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
D004988:Ethers, Cyclic; D007659:Ketones; D008674:Metals, Rare Earth; D009943:Organophosphorus Compounds; D013455:Sulfur; C005287:oxetane