Published TCIMAIL newest issue No.197
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Dehydration Agent for the Synthesis of Tetra-substituted Olefins
Bis(2,6-dimethylphenyl) chlorophosphate (1) is utilized in the formation of tetrasubstituted olefins by dehydration. When tertiary alcohols are treated with 1, the phosphate esters 2 are formed as an intermediate. Subsequent treatment of heat gives corresponding tetrasubstituted olefins in good yields with high stereoselectivity.1) Furthermore, this reaction has been used in the synthesis of tamoxifen, an antitumor compound. 1 is also used as a condensing agent for the synthesis of oligonucleotides with phosphorodithioates.2)
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References
- 1) Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach
- 2) Synthesis of oligonucleoside phosphorodithioates on a solid support by the H-phosphonothioate method
