Intermolecular double Prins-type cyclization: a facile and efficient synthesis of 1,6-dioxecanes.
Double or nothing: The title reaction converts a range of aromatic aldehydes and allenylmethyl/allyl silanes into 1,6-dioxecane derivatives in good to excellent yields (see scheme; Ar = aryl, Tf = triflate, THF = tetrahydrofuran, TMS = trimethylsilyl). In addition, the bisdiene product has been transformed into the corresponding tricyclic compound through a Diels-Alder reaction.
Ullapu
Punna Reddy
PR
Center for Chemoinformatics Research, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, South Korea.
Min
Sun-Joon
SJ
Chavre
Satish N
SN
Choo
Hyunah
H
Lee
Jae Kyun
JK
Pae
Ae Nim
AN
Kim
Youseung
Y
Chang
Moon Ho
MH
Cho
Yong Seo
YS
D000447:Aldehydes / Q000737:chemistry; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry
D000447:Aldehydes; D006571:Heterocyclic Compounds; D012821:Silanes