Synthesis of unsaturated esters from aldehydes: An inexpensive, practical alternative to the Horner-Emmons reaction under neutral conditions

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8125-8128

  Ledford, Brian E ^a   Carreira, Erick M ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; ESTER; REAGENT; SOLVENT;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030694238     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10182-4     Document Type: Article

References (20)

1. (a) Asymmetric Synthesis, Morrison, J. D., Ed; Academic: Orlando, 1985, Chapter 7, p 194.
2. (b) Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993, Chapter 4, p 103.
3. (a) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651.
4. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081.
5. Charette, A. B.; Pereira de Freitas-Gil, R. Tetrahedron Lett. 1997, 38, 2809.
6. For a general review of polyol syntheses, see: Ager, D. J.; East, M. B. Tetrahedron 1992, 48, 2803.
7. Nicolaou, K. C.; Daines, R. A.; Ogawa, Y.; Chakraborty, T. K. J. Am. Chem. Soc. 1988, 110, 4696, and references therein.
8. (a) Barrett, A. G. M.; Kasdorf, K. J. Am. Chem. Soc. 1996, 118, 11030.
9. (b) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357.
10. Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181.
11. (a) Herrmann, W. A.; Roesky, P. W.; Wang, M.; Scherer, W. Organometallics 1994, 13, 4531.
12. (b) Herrmann, W. A.; Wang, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1641.
13. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
14. With the exception of enoates in Entries 5, 6, 8, 10 and that in Eq 2, the enoate products are known: (a) Entry 1, Nonnemacher, A.; Mayer, R.; Plienger, H. Liebigs Ann. Chem. 1983, 2135.
15. (b) Entries 2&3, Vedejs, E.; Fleck, T. S. J. Am. Chem. Soc. 1989, 111, 5861.
16. (c) Entry 4, Takahashi, H.; Fujiwara, K.; Ohta, M. Bull. Chem. Soc. Jpn. 1962, 35, 1498.
17. Entry 7, Sundberg, R. J.; Bukowick, P. A.; Holcombe, F. U. J. Org. Chem. 1967, 32, 2938.
18. (e) Entry 9, Takano, S.; Kurotaki, A.; Takahashi, M.; Ogasawara, K. Synthesis 1986, 403.
19. 2Me followed by transesterification with NaOEt/EtOH.
20. f = 0.55, 6:1 hexanes/ethyl acetate) to give 470 mg of ethyl (E)-5-phenyl-2-pentenoate (95 % yield, 2.3 mmol).