The use of 1,4-dichlorobut-2-ene as a synthetic equivalent of 4-bromo- but-1-ene

Synlett

Volumn , Issue 6, 2000, Pages 835-837

  Hughes, Gregory ^a   Lautens, Mark ^a   Wu, Jingxiao ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Alkenes; Allylations; Amino acids; Lactones; Palladium catalysis

Indexed keywords

ALKENE; AMINO ACID; CHLORIDE; LACTONE; PALLADIUM;

ARTICLE; CATALYST; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034122357     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. References which make use of 1 or 2 to butenylate a variety of nucleopliles: a) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427.
2. b) Uenishi, J.; Tatsumi, Y.; Kobayashi, N.; Yonemitsu, O. Tetrahedron Lett. 1995, 36, 5909.
3. c) Molander, G.A.; Cameron, K.O. J. Org. Chem. 1993, 58, 5931.
4. Aldrich's 1999 catalogue quotes prices for 1, 2 (R = H) and 3 as $1,088.91/ mol, $432.44/ mol and $20.7/ mol respectively. All prices listed are in Canadian dollars for the largest available denomination. It should be noted that 3 does pose a health risk and should be handled with caution.
5. a) Tsuji, J.; Mandai, T. Synthesis 1996, 1.
6. b) Tsuji, J.; Minami, I.; Shimizu, I. Synthesis 1986, 623.
7. Shimizu, I.; Aida, F. Chem. Lett. 1988, 601.
8. A similar approach has been utilized by Tsuji using differentially functionalized butenediol (one oxygen as a carbonate, the other as an acetate), but this material must be prepared in two steps and the approach is only suitable for nucleophiles which can be allylated using Pd catalysis. Takahashi, T.; Miyazawa, M.; Ueno, H.; Tsuji, J. Tetrahedron Lett. 1986, 27, 3881.
9. a) Harding, K. E.; Nam, D. Tetrahedron Lett. 1988, 29, 3793-3796.
10. b) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z. J. Am. Chem. Soc. 1988, 110, 3994.
11. Moderate yields (50-57%) were reported for the butenylation of two compounds similar to 8 using 3 eq. of 1 or 1.3 eq. butenyltriflate respectively. See Ref. 1a.
12. a) Tetrahedron Symposia-in-Print No. 50 1993, 49, (17), 3433.
13. b) Miller, S.J.; Grubbs, R.H. J. Am. Chem. Soc. 1995, 117, 5855.
14. th International Symposium on Olefin Metathesis and Related Chemistry: Kerkrade, The Netherlands 1999, L19, pg. 34.
15. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
16. Lautens, M.; Hughes, G. Angew. Chem. Int. Ed. Engl. 1999, 38, 129.
17. There has been one report in the literature regarding the butenylation of δ-valerolactone in moderate yield (34%) using butenyliodide, which had to be prepared in 61% yield from 1. Fry, A.J.; Little, R.D.; Leonetti, J. J. Org. Chem. 1994, 59, 5017.
18. 2 evolution is also normally observed as the reaction mixture warms. The products were isolated by standard aqueous workup, followed by either flash chromatography or distillation.