The undesirable lability of tert-butyldimethylsilyl ethers under Pd/C-catalyzed hydrogenation conditions and solution of the problem by using a Pd/C(en) catalyst

Author:

Hattori Kazuyuki,Sajiki Hironao,Hirota Kosaku

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference16 articles.

1. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.

2. Selected reviews: (a) Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; pp. 113–148. (b) Kocienski, P. J. In Protecting Group; Thieme: Stuttgart, 1994; pp. 28–42.

3. While a removal of the TBDMS group from primary and secondary hydroxy groups by catalytic transfer hydrogenolysis (CTH) using PdO as a catalyst in refluxing cyclohexene–methanol have been reported (see below), deprotection of the TBDMS group under the hydrogenation conditions using Pd/C has not been reported to our best knowledge; see, Cormier, J. F.; Isaac, M. B.; Chen, L.-F. Tetrahedron Lett. 1993, 34, 243.

4. Honda, T.; Ishikawa, F. Synth. Commun. 1999, 29, 3323.

5. Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Soc., Perkin Trans. 1 1992, 2997.

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