TPM: A new protecting group for alkynes

Tetrahedron Letters

Volumn 40, Issue 45, 1999, Pages 7861-7865

  Haskel, Ariel ^a,b   Keinan, Ehud ^a,b  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Alkynes; Amides; Platinum; Platinum compounds; Protecting groups

Indexed keywords

ACETYLENE; ALKYNE; CARBON MONOXIDE; CHROMIC ACID; PLATINUM; PLATINUM DERIVATIVE;

ARTICLE; CATALYSIS; HYDROGENATION; MOLECULAR STABILITY; OXIDATION;

EID: 0033527597     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01537-3     Document Type: Article

References (20)

1. It has been shown that terminal alkynes can be protected by silylation. This method permits selective catalytic hydrogenation of mono- and disubstituted olefins. Palmer, C. J.; Casida, J. E. Tetrahedron Lett. 1990, 31, 2857.
2. (a) Nicholas, K. M.; Pettit, R. Tetrahedron Lett. 1971, 37, 3475.
3. (b) Seyferth, D.; Nestle, M. O.; Wehman, A. T. J. Am. Chem. Soc. 1975, 97, 7417.
4. Greenfield, H.; Sternberg, H. W.; Friedel, R. A.; Wotiz, J. H.; Markby, R.; Wender, I. J. Am. Chem. Soc. 1956, 78, 120.
5. 6(alkyne) using either diimide or borane/acetic acid (Ref. 2a).
6. Dickson, R. S.; Kirsch, H. P. Aust. J. Chem. 1972, 25, 1815.
7. (a) Clark, H. C.; Manzer, L. E. J. Am. Chem. Soc. 1973, 95, 3812.
8. (b) Clark, H. C.; Manzer, L. E. Inorg. Chem. 1974, 13, 1291.
9. For the preparation of (COD)PtMeCl, see: Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411.
10. +).
11. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, California, 1987; Ch. 4.
12. Manzer, L. E.; Meakin, P. Z. Inorg. Chem. 1976, 15, 3117.
13. These compounds were required for our ongoing research project, which involves catalytic antibodies: Haskel, A.; Keinan, E. 217th ACS National Meeting, Anaheim, CA, March 21-25, 1999, ORGN-073.
14. Coppola, G. M.; Damon, R. E. Synth. Commun. 1993, 23, 2003.
15. +).
16. +). Mp=58-60°C.
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20. +).