Tandem alkylation-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,6-tetrasubstituted tetrahydropyrans.
A stereoselective method for the synthesis of substituted tetrahydropyran derivatives employing a tandem S(N)2-Michael addition sequence to vinylogous carbonates is developed. The method is extended to the synthesis of bicyclic ether motifs present in polyether ladder toxins.
Gharpure
Santosh J
SJ
Department of Chemistry, Indian Institute of Technology Madras, Chennai - 600036, India. sjgharpure@iitm.ac.in
Reddy
S Raja Bhushan
SR
D000478:Alkylation; D018360:Crystallography, X-Ray; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D004988:Ethers, Cyclic; D011714:Pyrans; D014753:Vinyl Compounds