Amine-Catalyzed Aldol Condensation in the Presence of Lithium Perchlorate

Abstract

A catalytic aldol condensation in the presence of lithium perchlorate and tertiary amines is described giving pure products in high yields. The aldol condensation can be performed even in the presence of hydrated lithium perchlorate.

aldol reactions - aldehydes - ketones - catalysis - amines

References

1a Nakano T. Irifune S. Inada A. J. Org. Chem.  1987,  52:  2239 

1b Ogawa M, Ishii Y, Nakano T, and Irifune S. inventors; Jpn. Kohai Tokkyo JP  63192446 A2.  ; Chem. Abstr. 1988, 63, 238034

2 Deli J. Lorand T. Szabo D. Foldesi A. Pharmazie  1984,  39:  539 

3 Kishore G. Kishore K. Polymer  1995,  36:  1903 

4a Adams KB. Ferstl EM. Davis MC. Herold M. Kurtkaya S. Camalier RF. Hollingshead MG. Kaur G. Sausville EA. Rickles FR. Snyder JP. Liotta DC. Shoji M. Bioorg. Med. Chem.  2004,  12:  3871 

4b Robinson TP. Hubbard RB. Ehlers TJ. Arbiser JL. Goldsmith DJ. Bown JP. Bioorg. Med. Chem.  2005,  13:  4007 

5 Clarke TP. Höppe HAF. Lloyd-Jones GC. Murray M. Peakman TM. Stentiford RA. Walsh KE. Worthington PA. Eur. J. Org. Chem.  2000,  963 

6 Arcadi A. Bianchi G. Chiarini M. Dànniballe G. Marinelli F. Synlett  2004,  944 

7 Fairlamb IJS. Kapdi AR. Lee AF. Org. Lett.  2004,  6:  4435 

8

Compound 4d: 1 g costs 600 $ (TRC Biomedical Research Chemicals).

9a Ti(OR)₄: Mahrwald R. Schick H. Synthesis  1990,  592 

9b RuCl₃: Iranpoor N. Kazemi F. Tetrahedron  1998,  54:  9475 

9c SmI₃: Bao WL. Zhang YM. Youji Huaxue  1998,  18:  272 

9d FeCl₃: Zhang Fan XS. Niu HY. Wang JJ. Green Chem.  2003,  5:  267 

9e BF₃·Et₂O: Huang DF. Wang JX. Hu YL. Chem. Lett.  2003,  14:  333 

9f InCl₃: Deng G. Ren T. Synth. Commun.  2003,  33:  2995 

9g Yb(OTf)₃: Wang L. Scheng J. Han HT. Fan Z. Qian C. Synthesis  2004,  3060 

9h For NaOH/H₂O-system, see: Fairlamb IJS. SyntheticPages  2004,  221 

10 Markert M. Mahrwald R. Synthesis  2004,  1429 

11 For safety information, see: Armarego WLF. Perrin DD. Purification of Laboratory Chemicals   Butterworth-Heinemann; Oxford: 1997. 

12 Ramalingam K. Berlin KD. Satyamurthy N. Sivakumar R. J. Org. Chem.  1979,  44:  471 

13 Shoppee CW. Cooke BJA. J. Chem. Soc., Perkin Trans. 1  1973,  1026 

14a Wattanasin S. Murphy WS. Synthesis  1980,  647 

14b Suarez JAQ, Peseke K, Kordian M, Carvalho JE, Kohn LK, Antonio MA, and Brunhari H. inventors; PCT Int. Appl.  2004047716.  (4d, 87% yield)

15 Thiele G. Streitwieser A. J. Am. Chem. Soc.  1994,  116:  446 

16a Ocafrain M. Devaud M. Troupel M. Perichon J. J. Chem. Soc., Chem. Commun.  1995,  2331 

16b Binder J. Zbiral E. Tetrahedron Lett.  1984,  25:  4213 

17 Frey H. Behmann G. Kaupp G. Chem. Ber.  1987,  120:  387 

18 Kaupp G. Frey H. Behmann G. Chem. Ber.  1988,  121:  2127 

19 Eldin S. Whalen DL. Pollack RM. J. Org. Chem.  1993,  58:  7100