Alkynyltrifluoroborates as versatile tools in organic synthesis: a new route to spiroketals.
[reaction: see text] A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.
Doubský
Jan
J
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic.
Streinz
Ludvík
L
Saman
David
D
Zedník
Jirí
J
Koutek
Bohumír
B
D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D001896:Boron Compounds; D013141:Spiro Compounds; D010165:Palladium; D008094:Lithium