Reaction of the lithio-derivative of methoxy allene with SAMP- hydrazones: Access to enantiopure 3-pyrrolines

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5009-5012

  Breuil Desvergnes, Valérie ^a   Compain, Philippe ^a   Vatèle, Jean Michel ^a   Goré, Jacques ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; HYDRAZONE DERIVATIVE;

AMINATION; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; ENANTIOMER; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0033516552     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00934-X     Document Type: Article

References (16)

1. - For recent preparations of 3 pyrrolines, see : a) Hassner, A.; Balasubramanian, T. Tetrahedron Lett. 1996, 37, 5755-5758.
2. b) Xu, Z; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464 and J.Org.Chem.1998, 63, 5031-5041.
3. b) Xu, Z; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464 and J.Org.Chem.1998, 63, 5031-5041.
4. c) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett 1999, 228-230.
5. - Rochet, P.; Vatèle, J.M.; Goré, J. Synlett 1993, 105-107.
6. - Surivet, J.P.; Goré, J.; Vatèle, J.M. Tetrahedron 1996, 52, 14877-14890.
7. - a) Enders, D.; Schubert, H.; Nübling, C. Angew. Chem.Int.Ed. 1996, 25, 1109-1114.
8. b) Enders, D.; Nubling, C.; Schubert, H. Liebigs Ann./Recueil 1997, 1115-1123.
9. c) For a review on asymetric synthesis by addition of organometallic reagent to CN double bonds, see Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
10. - The SAMP-hydrazines 5 are unstable under chromatographic conditions. The isomeric pyrrolines 6 may be purified by flash-chromatography.
11. 1H NMR and by gas chromatography.
12. - The configuration of compounds 5 and 6 given is in accordance with the stereochemistry proposed by Enders et al. for the addition of organolithium reagents to SAMP-hydrazones; see ref. 4b.The relative stereochemistry of 6a has been confirmed by X-ray analysis of a single crystal.
13. - The use of large excess of organolithium reagent in their reaction with SAMP-hydrazones is commonplace, for example see Enders, D.; Lochtman, R.; Synlett 1997, 355-356.
14. - The cyclisation of α-allenic amines to 3-pyrrolines has been previously decribed : Claesson, A.; Sahlberg C.; Luthman K. Acta Chem. Scand. 1979, 309-310.
15. - SMP may be quantitatively recovered allowing the chiral auxiliary to be recycled.
16. 3 )) only one signal was observed.