Intermolecular [3+2] MIRC reactions with alkynoates. Asymmetric Michael addition leading to a nonracemic cyclopentene-annulated α,β-butenolide

Tetrahedron Letters

Volumn 41, Issue 29, 2000, Pages 5583-5587

  Nakache, Philippe ^a   Ghera, Eugene ^a   Hassner, Alfred ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

Asymmetric induction; Butenolides; Cyclopentenecarboxylates; Lithium ion chelation; Michael reactions

Indexed keywords

BUTENOLIDE; CYCLOPENTENE DERIVATIVE; LITHIUM ION;

ALKYLATION; ARTICLE; CHELATION; CHIRALITY; DRUG SYNTHESIS; MOLECULAR INTERACTION; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0034661882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00867-4     Document Type: Article

References (26)

1. Stereochemistry. Part 91. For part 90 see: Gottlieb, L.; Hassner, A. Synth. Commun. 2000, in press.
2. For reviews, see: Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp. 287-313; Hudlicky, T. Chem. Rev. 1989, 89, 1457.
3. For reviews, see: Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp. 287-313; Hudlicky, T. Chem. Rev. 1989, 89, 1457.
4. Ghera, E.; Yechezkel, Y.; Hassner, A. J. Org. Chem. 1996, 61, 4959, and references cited therein.
5. Yechezkel, T.; Ghera, E.; Hassner, A. Tetrahedron: Asymmetry 1996, 2422.
6. Binger, P.; Buch, H. M. Top Curr. Chem. 1987, 135, 77; Binger, P.; Lu, Q.-H.; Wedemann, P. Angew. Chem., Int. Ed. Engl. 1985, 24, 316.
7. Binger, P.; Buch, H. M. Top Curr. Chem. 1987, 135, 77; Binger, P.; Lu, Q.-H.; Wedemann, P. Angew. Chem., Int. Ed. Engl. 1985, 24, 316.
8. Yamago, S.; Ejiri, S.; Nakamura, E. Angew. Chem., Int. Ed. Engl. 1995, 34, 2154; see also: van der Louw, J.; van der Baan, F.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1987, 28, 2889.
9. Yamago, S.; Ejiri, S.; Nakamura, E. Angew. Chem., Int. Ed. Engl. 1995, 34, 2154; see also: van der Louw, J.; van der Baan, F.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1987, 28, 2889.
10. Trost, B. M.; Balkovek, J. M.; Angle, S. R. Tetrahedron Lett. 1986, 27, 1445.
11. Breuilles, P.; Uguen, D. Tetrahedron Lett. 1987, 28, 6053.
12. 4Cl) after all the alkynoate reacted (TLC). The crude product, after extraction with ether, was rapidly filtered via a short silica column (ethyl acetate-ether) to separate unreacted 2 and the polymerized polar material and then purified by silica gel (flash) chromatography (petroleum ether-ethyl acetate).
13. Reaction of 2 with unsubstituted ethyl propiolate afforded, however, the open-chain adduct; see also: Alonso, D. A.; Flavello, L. R.; Mancheno, B.; Najera, C.; Tomas, M. J. Org. Chem. 1996, 61, 5004.
14. Stabilized carbanions are poor donors for intermolecular Michael reactions with γ-alkyl or aryl ynoates unless the adduct intermediate is trapped by strong electrophiles: see, e.g.: Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p. 41; Bury, A.; Joay, S. D.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1986, 124.
15. Stabilized carbanions are poor donors for intermolecular Michael reactions with γ-alkyl or aryl ynoates unless the adduct intermediate is trapped by strong electrophiles: see, e.g.: Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p. 41; Bury, A.; Joay, S. D.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1986, 124.
16. For the preparation of a similar ester, see: Boeckman, R. K.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1991, 113, 5337.
17. 3) δ=1.41 (s, 3H), 1.63 (s, 3H), 3.19 (dq, J=18.2, 2.4 Hz, 1H), 3.29 (d, J=19.3 Hz, 1H), 4.26 (dd, J=7.20, 7.10 Hz, 1H), 4.47 (t, J=7.19 Hz, 1H), 4.71 (s, 1H), 5.12 (s, 2H), 5.52 (t, J=7.1 Hz, 1H), 7.05-7.13 (m, 2H), 7.26 (m, 1H), 7.42 (m, 2H), 7.57 (m, 2H), 7.66-7.71 (m, 1H), 7.86-7.89 (m, 2H).
18. Ghera, E.; Kleiman, V.; Hassner, A. J. Org. Chem. 1999, 64, 8; for subsequent similar observations, see: Juaristi, E.; Leon-Romo, J. L.; Ramirez-Quiros, Y. J. Org. Chem. 1999, 64, 2914; Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050.
19. Ghera, E.; Kleiman, V.; Hassner, A. J. Org. Chem. 1999, 64, 8; for subsequent similar observations, see: Juaristi, E.; Leon-Romo, J. L.; Ramirez-Quiros, Y. J. Org. Chem. 1999, 64, 2914; Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050.
20. Ghera, E.; Kleiman, V.; Hassner, A. J. Org. Chem. 1999, 64, 8; for subsequent similar observations, see: Juaristi, E.; Leon-Romo, J. L.; Ramirez-Quiros, Y. J. Org. Chem. 1999, 64, 2914; Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050.
21. 2.
22. 3) exhibits a long range interaction between the C=O group (δ 161.1) and one of the protons of the oxymethylene group (δ 4.56) which is missing in the spectrum of 7; other spectral data agree with the given structure.
23. 3): δ 2.52 (s, 3H), 3.44 (t, J=3.1 Hz, 2H), 5.10 (t, J=3.1 Hz, 2H), 7.58-7.94 (m, 5H).
24. In contrast with the well-known effects of Li cation coordination with heteroatoms, the influence of Li-Cl coordination was not sufficiently explored; see, however: Gschwend, H. W.; Rodriguez, H. R. In Org. Reactions; Vol. 26, 1979; pp. 74-75; Najera, C.; Sansano, J. M. Tetrahedron Lett. 1992, 33, 6543. For an example of F-Li coordination effects, see: Gilday, J. P.; Widdowson, D. A. Tetrahedron Lett. 1986, 27, 5525. We are indebted to Prof. G. H. Posner for valuable comments.
25. In contrast with the well-known effects of Li cation coordination with heteroatoms, the influence of Li-Cl coordination was not sufficiently explored; see, however: Gschwend, H. W.; Rodriguez, H. R. In Org. Reactions; Vol. 26, 1979; pp. 74-75; Najera, C.; Sansano, J. M. Tetrahedron Lett. 1992, 33, 6543. For an example of F-Li coordination effects, see: Gilday, J. P.; Widdowson, D. A. Tetrahedron Lett. 1986, 27, 5525. We are indebted to Prof. G. H. Posner for valuable comments.
26. In contrast with the well-known effects of Li cation coordination with heteroatoms, the influence of Li-Cl coordination was not sufficiently explored; see, however: Gschwend, H. W.; Rodriguez, H. R. In Org. Reactions; Vol. 26, 1979; pp. 74-75; Najera, C.; Sansano, J. M. Tetrahedron Lett. 1992, 33, 6543. For an example of F-Li coordination effects, see: Gilday, J. P.; Widdowson, D. A. Tetrahedron Lett. 1986, 27, 5525. We are indebted to Prof. G. H. Posner for valuable comments.