Stereoselective Reduction of Conjugated Homopropargylic Alcohols to (E)-Homoallylic Alcohols by Sodium Bis(2-methoxyethoxy) Aluminium Hydride

Synlett

Volumn 1997, Issue 8, 1997, Pages 992-994

  Crousse, Benoit ^a   Alami, Mouâd ^a   Linstrumelle, Gérard ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002757598     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-926     Document Type: Article

References (30)

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13. Red-Al® is an efficient reagent for the reduction of propargylic alcohols into (E)-allylic alcohols see: Denmark, S.E.; Jones, T.K. J. Org. Chem. 1982, 47, 4595. For a review see: Gugelchuk, M. Sodium Bis(2-methoxyethoxy)aluminium Hydride in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.; Ed., Wiley, Chichester 1995, 7, 4518.
14. Red-Al® is an efficient reagent for the reduction of propargylic alcohols into (E)-allylic alcohols see: Denmark, S.E.; Jones, T.K. J. Org. Chem. 1982, 47, 4595. For a review see: Gugelchuk, M. Sodium Bis(2-methoxyethoxy)aluminium Hydride in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.; Ed., Wiley, Chichester 1995, 7, 4518.
15. Brandsma, L. "Preparative Acetylenic Chemistry": 2nd Ed., Elsevier, 1988, pp. 220.
16. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763.
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21. For a review see: (e) Linstrumelle, G.; Alami, M. (E) and (Z)-dichloroethylene in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.; Ed., Wiley, Chichester 1995, 3, 1710.
22. 3) δ 135.40, 133.40, 132.05, 130.15, 130.00, 129.10, 61.95, 36.15, 32.75, 31.35, 29.00, 22.50, 14.00.
23. 3) δ 141.45, 133.40, 132.10, 131.25, 128.15, 127.90, 123.25, 109.70, 91.55, 88.85, 61.55, 36.00.
24. For a review see: Rychnovsky, S.D. Chem. Rev. 1995, 95, 2021.
25. 4, at 0°C, the reduction of 1k was not stereoselective and led directly to desilylated compounds 5 as a mixture of stereoisomers (63%, 3E,5Z/3E,5E : 89/11).
26. 7c
27. Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109.
28. 2) λ = 311 nm (ε = 49000).
29. Boland, W.; Schroer, N.; Sieler, C.; Feigel, M. Helv. Chim. Acta. 1987, 70, 1025.
30. max = 49500); mp : 118-120°C.