Stannane-free chemoselective hydrodehalogenation of 4-halotetrahydropyrans: scope and application to natural product synthesis.
A stannane-free hydrodehalogenation of 4-halotetrahydropyran under very mild conditions has been developed. This methodology allows selective one-pot dehalogenation and/or debenzylation depending on the type of halide-substrate used. The applicability of this methodology is well demonstrated in the synthesis of a key intermediate toward the enantioselective synthesis of (+)-SCH 351448.
Chan
Kok-Ping
KP
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616.
Ling
Yvonne Hui
YH
Chan
Jocelyn Li-Ting
JL
Loh
Teck-Peng
TP
D001688:Biological Products / Q000138:chemical synthesis*; D006219:Halogens / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis; D008722:Methods; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism; D017971:Tin Compounds
D001688:Biological Products; D006219:Halogens; D007783:Lactones; D011714:Pyrans; C451479:SCH 351448; D017971:Tin Compounds; C031525:stannane