Triethyl- (or trimethyl-)silyl triflate-catalyzed reductive cleavage of triphenylmethyl (trityl) ethers with triethylsilane

Hiroshi Imagawa; Tomoko Tsuchihashi; Rajesh K Singh; Hirofumi Yamamoto; Takumichi Sugihara; Mugio Nishizawa

doi:10.1021/ol0271988

Triethyl- (or trimethyl-)silyl triflate-catalyzed reductive cleavage of triphenylmethyl (trityl) ethers with triethylsilane

Org Lett. 2003 Jan 23;5(2):153-5. doi: 10.1021/ol0271988.

Authors

Hiroshi Imagawa¹, Tomoko Tsuchihashi, Rajesh K Singh, Hirofumi Yamamoto, Takumichi Sugihara, Mugio Nishizawa

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.

PMID: 12529128
DOI: 10.1021/ol0271988

Abstract

[reaction: see text] A triphenylmethyl (trityl) ether was reductively and instantaneously cleaved by triethylsilane in the presence of a catalytic amount of TES- (or TMS)-triflate. The reaction conditions are mild enough to achieve reduction in the presence of a variety of acid-sensitive functional groups. Upon a mild acidic treatment of the crude product, the corresponding alcohol is obtained in high yield.