TY - JOUR
T1 - Dimethylthiocarbamate (DMTC)
T2 - An Alcohol Protecting Group
AU - Barma, D. K.
AU - Bandyopadhyay, A.
AU - Capdevila, Jorge H.
AU - Falck, J. R.
PY - 2003/12/11
Y1 - 2003/12/11
N2 - (Equation Presented) Dimethylthiocarbamates (DMTCs), prepared from the corresponding alcohols using commercial dimethylthiocarbamoyl chloride, are spectrally simple, achiral, and nonpolar. DMTCs are moderately to highly stable to a wide range of reagents and conditions including metal hydrides, hydroboration, ylides, NaOH, HCl, organolithiums, Grignards, DDQ, PCC, Swern, n-Bu4NF, CrCl2, heat, and Lewis acids. They are readily removed by NalO4 or H2O2 in the presence of other common alcohol protecting groups.
AB - (Equation Presented) Dimethylthiocarbamates (DMTCs), prepared from the corresponding alcohols using commercial dimethylthiocarbamoyl chloride, are spectrally simple, achiral, and nonpolar. DMTCs are moderately to highly stable to a wide range of reagents and conditions including metal hydrides, hydroboration, ylides, NaOH, HCl, organolithiums, Grignards, DDQ, PCC, Swern, n-Bu4NF, CrCl2, heat, and Lewis acids. They are readily removed by NalO4 or H2O2 in the presence of other common alcohol protecting groups.
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U2 - 10.1021/ol0354573
DO - 10.1021/ol0354573
M3 - Article
C2 - 14653666
AN - SCOPUS:0347228972
SN - 1523-7060
VL - 5
SP - 4755
EP - 4757
JO - Organic Letters
JF - Organic Letters
IS - 25
ER -