Debenzylation using catalytic hydrogenolysis in trifluoroethanol, and the total synthesis of (−)-raumacline

…, HPT Dang, TR Phillips, RA Price, JH Whittaker

Index: Bailey, Patrick D.; Beard, Mark A.; Dang, Hoa P.T.; Phillips, Theresa R.; Price, Richard A.; Whittaker, James H. Tetrahedron Letters, 2008 , vol. 49, # 13 p. 2150 - 2153

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Citation Number: 19

Abstract

N-Debenzylations using catalytic hydrogenolysis often fail to take place unless alcoholic solvents are used, but this can lead to N-alkylation as a side reaction; using trifluoroethanol as the solvent overcomes this problem, and leads to highly reliable hydrogenolyses for a wide range of substrates, including the final deprotection step in our total synthesis of (−)- raumacline.