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⁾

Related Product

B1922

Bis(2,6-dimethylphenyl) Chlorophosphate

References

• 1) Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach
  • N.-K. Lim, P. Weiss, B. X. Li, C. H. McCulley, S. R. Hare, B. L. Bensema, T. A. Palazzo, D. J. Tantillo, H. Zhang, F. Gosselin, Org. Lett. 2017, 19, 6212.
• 2) Synthesis of oligonucleoside phosphorodithioates on a solid support by the H-phosphonothioate method
  • K. Kamaike, K. Hirose, Y. Kayama, E. Kawashima, Tetrahedron 2006, 62, 11814.

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