A practical, versatile difluorovinylcopper reagent

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5975-5978

  Crowley, P J ^b   Howarth, J A ^d   Owton, W M ^c   Percy, J M ^a   Stansfield, K ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

^c ELI LILLY AND COMPANY   (United States)

^d LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; CARBAMIC ACID DERIVATIVE; COPPER DERIVATIVE; LITHIUM CHLORIDE; REAGENT; TRIFLUOROETHANOL; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS; TEMPERATURE SENSITIVITY; THERMOSTABILITY;

EID: 0000651413     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01179-3     Document Type: Article

References (16)

1. 1. Howarth, J.A.; Owton, W.M.; Percy, J.M; Rock, M.; Tetrahedron, 1995, 51, 10289-10302. See also, Lee, J.; Tsukazaki, T.; Snieckus, V.; Tetrahedron Lett., 1993, 34, 415-418.
2. 1. Howarth, J.A.; Owton, W.M.; Percy, J.M; Rock, M.; Tetrahedron, 1995, 51, 10289-10302. See also, Lee, J.; Tsukazaki, T.; Snieckus, V.; Tetrahedron Lett., 1993, 34, 415-418.
3. 2. Burton, D.J.; Yang, Z.Y.; Morken, P.A.; Tetrahedron, 1994, 50, 2993-3063.
4. 3. Methods based on the corresponding zinc reagents failed in our hands; see Gillet, J.P.; Sauvêtre, R.; Normant, J.F.; Synthesis, 1986, 538-543.
5. 4. Alexakis, A.; Mutti, S.; Normant, J.F.; J. Am. Chem. Soc., 1991, 113, 6322-6324.
6. 5. The procedure described recently by Reetz and Kindler was followed. Reetz, M.T.; Kindler, A.; J. Chem. Soc., Chem. Commun., 1994, 2509-2510.
7. 6. Metallated fluoroalkenes darken dramatically when allowed to warm above a critical temperature. In the case of the transmetallated species, that temperature clearly lies above 15°C.
8. ¶ In the case of acid chloride electrophiles, the reactions were run for 4 hours before work-up, rather than overnight.
9. 8. Sengupta, S.; Snieckus, V.; J. Org. Chem., 1990, 55, 3982-3983.
10. 9. Ley, S.V.; Woods, M.; Zanittigerosa, A.; Synthesis, 1992, 52-54.
11. +).
12. 11. Ichikawa, J.; Kobayashi, M.; Yokota, N.; Minami, T.; Tetrahedron, 1994, 50 11637-11646.
13. 12. Taylor, R.J.K.; Casy, G.; in "Organocopper Reagents: A Practical Approach", ed. by Taylor, R.J.K.; Oxford University Press, Oxford, 1994, Chapter 2, 38.
14. 2: 4a, 42%; 4b, 35%; 4c, 40%; 4d, 25%.
15. 14. Percy, J.M.; Contemp. Org. Synth.; 1995, 4, 251-268.
16. 15. Patel, S.T.; Percy, J.M.; Wilkes, R.D.; J. Org. Chem., 1996, 61, 166-173 and references therein.