Neopentyl and neophyl groups: New nontransferable groups for organocopper and organozinc chemistry

Synthesis

Volumn , Issue 2, 1999, Pages 312-316

  Lutz, Christian ^a   Jones, Philip ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Asymmetric synthesis; Conjugate addition; Mixed zinc reagents; Nontransferable groups; Organocuprates

Indexed keywords

ALKENE DERIVATIVE; COPPER DERIVATIVE;

ARTICLE; ENANTIOMER; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0032982020     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3387     Document Type: Article

References (22)

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2. Knochel, P.; Almena Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
3. Berger, S.; Langer, F.; Lutz, C.; Knochel, P.; Mobley, T. A.; Reddy, C. K. Angew. Chem. 1997, 109, 1603-1605; Angew. Chem., Int. Ed. Engl. 1997, 36, 1496. Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895 Jones, P.; Knochel, P. J. Chem. Soc., Perkin Trans, 1 1997, 3117.
4. Berger, S.; Langer, F.; Lutz, C.; Knochel, P.; Mobley, T. A.; Reddy, C. K. Angew. Chem. 1997, 109, 1603-1605; Angew. Chem., Int. Ed. Engl. 1997, 36, 1496. Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895 Jones, P.; Knochel, P. J. Chem. Soc., Perkin Trans, 1 1997, 3117.
5. Berger, S.; Langer, F.; Lutz, C.; Knochel, P.; Mobley, T. A.; Reddy, C. K. Angew. Chem. 1997, 109, 1603-1605; Angew. Chem., Int. Ed. Engl. 1997, 36, 1496. Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895 Jones, P.; Knochel, P. J. Chem. Soc., Perkin Trans, 1 1997, 3117.
6. Berger, S.; Langer, F.; Lutz, C.; Knochel, P.; Mobley, T. A.; Reddy, C. K. Angew. Chem. 1997, 109, 1603-1605; Angew. Chem., Int. Ed. Engl. 1997, 36, 1496. Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895 Jones, P.; Knochel, P. J. Chem. Soc., Perkin Trans, 1 1997, 3117.
7. Jones, P. Reddy, C. K.; Knochel, P. Tetrahedron 1998, 54, 1471.
8. Trimethylsilylmethyl lithium and trimethylsilylmethyl chloride are both commercially available.
9. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691.
10. Schrock, R. R.; Fellman, J. D. J. Am. Chem. Soc. 1978, 100, 3359.
11. For the preparation of some other mixed diorganozincs see: (a) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449. (b) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans, 1 1990, 937.
12. For the preparation of some other mixed diorganozincs see: (a) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449. (b) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans, 1 1990, 937.
13. For the preparation of some other mixed diorganozincs see: (a) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449. (b) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans, 1 1990, 937.
14. Wissing, E.; Kleijn, H.; Boersma, J.; van Koten, G. Recl. Trav. Pays-Bas 1993, 112, 618.
15. For the use of mixed methyl(alkyl)zinc in synthesis see ref. 6a
16. For the use of diorganozincs in 1,4-addition ractions see: Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495.
17. Cano, A.; Cuenca, T.; Galakhov, M.; Rodríguez, G. M.; Royo, P.; Cardin, C. J.; Convery, M. A. J. Organomet. Chem. 1995, 493, 17.
18. Organocopper Reagents: A Practical Approach, Taylor, R. J. K., Ed.; Harwood, L. M.; Moody, C. J., Series Eds.; Oxford, 1994.
19. Bertz has prepared and investigated the reactivity of alkyl (trimethylsilylmethyl)cuprates and argues the involvement of β-silyl effect. Bertz, S. H.; Eriksson, M.; Miao, G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 10906 and references therein.
20. Ostwald, R.; Chavant, P. -Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143.
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22. Nützel, K.; Houben-Weyl, Methoden Org. Chem., Thieme: Stuttgart, 1973, 13/2a, 553