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Practical synthesis of N-Boc- and N-Cbz-α-amido stannanes from α-amido sulfones using TMSSnBu3 and CsF. 2011

Tsuyoshi Mita, and Yuki Higuchi, and Yoshihiro Sato
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. tmita@pharm.hokudai.ac.jp

In the presence of TMSSnBu(3) and CsF, stannylation of N-Boc- and N-Cbz-α-amido sulfones proceeded very well to afford the corresponding α-amido stannanes in moderate-to-high yields. This reaction tolerated α-aryl-, alkenyl-, and alkyl-substituted α-amido sulfones as well as substrates containing either an ester or cyano moiety, which might be reactive with lithium or magnesium stannides employed in conventional stannylation.

UI MeSH Term Description Entries
D007097 Imines Organic compounds containing a carbon-nitrogen double bond where a NITROGEN atom can be attached to HYDROGEN or an alkyl or aryl group. Imine
D009947 Organotin Compounds Organic compounds which contain tin in the molecule. Used widely in industry and agriculture. Compounds, Organotin
D002586 Cesium A member of the alkali metals. It has an atomic symbol Cs, atomic number 55, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency. Caesium,Caesium-133,Cesium-133,Caesium 133,Cesium 133
D005459 Fluorides Inorganic salts of hydrofluoric acid, HF, in which the fluorine atom is in the -1 oxidation state. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Sodium and stannous salts are commonly used in dentifrices. Fluoride
D000588 Amines A group of compounds derived from ammonia by substituting organic radicals for the hydrogens. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amine
D013450 Sulfones Sulfone
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D017971 Tin Compounds Inorganic compounds that contain tin as an integral part of the molecule. Compounds, Tin

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