Chiral lithiomethyl ethers by DTBB-catalyzed chlorine-lithium exchange

Anales de Quimica

Volumn 93, Issue 1, 1997, Pages 44-48

  Ortiz, Javier ^a   Guijarro, Albert ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Arene catalyzed lithiation; Chiral lithiomethyl ethers; EPC synthesis; Menthyl derivatives

Indexed keywords

EID: 33749277875     PISSN: 11302283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. For a general monograph, see: Morrison JD (ed) (1983-1985) Asymmetric Synthesis, Vols 1-5. Academic Press Inc, New York
2. Morrison JD (1980) A Summary of Ways to Obtain Optically Active Compounds. In: Morrison JD (ed) Asymmetric Synthesis. Vol I, Academic Press Inc, New York, p 2
3. Seebach D, Hungerbühler E (1980) In: Scheffold R (ed) Modern Synthetics Methods. Salle+Sauerländer-Verlag, Aarau. and references therein
4. For the last paper from our laboratory on EPC-Synthesis. see: Bachki A. Foubelo F. Yus M (1995) Tetrahedron:Asymmetry 6:1907-1910
5. 5a Yus M. Ramon DJ ( 1991 ) J Chem Soc Chem Comm 398-400
6. b Yus M (1996) Chem Soc Rev 155-161
7. For a review, see: Nâjera C, Yus M ( 1991 ) Trends Org Chem 2:155-181
8. For the last paper from our laboratory on this topic, see: Guijarro A, Ortiz J. Yus M (1996) Tetrahedron Lett 37:5597-5600
9. For the last paper from our laboratory on this topic, sec: Guijarro A. Yus M ( 1996) Tetrahedron 52:797-1810
10. Guijarro A. Mancheno B. Orti? J. Yus M (1996) Tetrahedron 52:6431650
11. Guijarro A, Yus M ( 1996) Tetrahedron Lett .37:5593-5596
12. 1. For a monograph on the Barbier reaction, see: Blomberg C (1993) The Barbier Reaction and the Related One-Pot Processes. Springer-Verlag. Berlin
13. The preparation of this type of dl-reagents [12a) has been achieved at low temperature by three different processes depending on the starting materials: (1) Tin-lithium transmetallation [12b]; (2) Sulphur-lithium exchange |12c|: (3) Deprotonation of some ethers, esters or related compounds [ 12d]
14. a Seebach D (1979) Angew Chem Int Ed Engl 18:239-258
15. b See. for instance: Tomooka K. Igarashi T. Watanabe M. Nakai T (1992) Tetrahedron Lett 33:5795-5798 and references therein
16. See. for instance: Rychnovsky SD. Skalizky DJ (1992) J Org Chem 57:4336-4339. and references therein
17. See. for instance: Schwerdtfeger J. Hoppe D ( 1992) Angew Chem Int Ed Engl 31:1505-1507, and references therein
18. For compounds 2 and 5 was not possible to obtain the corresponding HRMS due to either very low intensity or absence of the M+ signal
19. This compound, which is commercially available (ACROS), can be easily prepared by a reported method: Shatzmiller S. Dolithzky B7. BaharE(1991) Liebigs Ann Chem 375-379
20. DTBB gave better results than naphthalene; see. reference 9. For a comparative study on the use of both arènes, see: Freeman PK, Hutchison LL (1980) J Org Chem 45:1924-1930
21. In general, non-stabilised u-lithioethers are unstable species even at low temperature due to their tendency to undergo cc-elimination [ 16a] or Wittig rearrangement | I6bl processes
22. a Schöllkopf U. Kuppers H ( 1964) Tetrahedron Lett 1503-1506
23. b Schöllkopf U (1970) Angew Chem Int Ed Engl 9:763-773
24. This behaviour has been already observed in other type of very reactive functionalised organolithium compounds. See. for instance: a Nâjera C. Yus M. Seebach D (1984) Helv Chim Acta 67:289-300
25. b See also reference 4 and literature cited therein