A catalytic and enantioselective desymmetrization of meso cyclic allylic bisdiethylphosphates with organozinc reagents

Angewandte Chemie - International Edition

Volumn 42, Issue 2, 2003, Pages 234-236

  Piarulli, Umberto ^a   Daubos, Philippe ^b   Claverie, Christelle ^b   Roux, Maryline ^b   Gennari, Cesare ^b  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Alkylation; Asymmetric synthesis; Copper; Organophosphates; Zinc

Indexed keywords

CATALYSIS; COPPER; OPTIMIZATION; ZINC COMPOUNDS;

ENANTIOMERS;

PHOSPHATES;

COPPER COMPLEX; PHOSPHATE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0037434168     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390088     Document Type: Article

References (32)

1. For a recent review, see: M. C. Willis, J. Chem. Soc. Perkin Trans. 1 1999, 1765-1784.
2. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
3. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
4. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
5. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
6. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
7. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
8. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
9. For leading examples of desymmetrization of meso cyclic allylic diol derivatives (esters, carbonates, and the closely related meso oxabicyclic alkenes), see: a) B. M. Trost, J. Dudash, Jr., E. J. Hembre, Chem. Eur. J. 2001, 7, 1619-1629; b) B. M. Trost, D. E. Patterson, E. J. Hembre, Chem. Eur. J. 2001, 7, 3768-3775; c) B. M. Trost, J. Dudash, Jr., O. Dirat, Chem. Eur. J. 2002, 8, 259-268; d) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805; e) M. Lautens, S. Hiebert, J.-L. Renaud, Org. Lett. 2000, 2, 1971-1973; f) M. Lautens, S. Hiebert, J.-L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839; g) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314, and references therein; h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
10. For copper-catalyzed allylic alkylations in the presence of dialkylzinc reagents, see: a) F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391-393; Angew. Chem. Int. Ed. 1999, 38, 379-381; b) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460; c) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171; d) S. Ongeri, U. Piarulli, M. Roux, C. Monti, C. Gennari, Helv. Chim. Acta 2002, 3388-3399.
11. For copper-catalyzed allylic alkylations in the presence of dialkylzinc reagents, see: a) F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391-393; Angew. Chem. Int. Ed. 1999, 38, 379-381; b) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460; c) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171; d) S. Ongeri, U. Piarulli, M. Roux, C. Monti, C. Gennari, Helv. Chim. Acta 2002, 3388-3399.
12. For copper-catalyzed allylic alkylations in the presence of dialkylzinc reagents, see: a) F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391-393; Angew. Chem. Int. Ed. 1999, 38, 379-381; b) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460; c) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171; d) S. Ongeri, U. Piarulli, M. Roux, C. Monti, C. Gennari, Helv. Chim. Acta 2002, 3388-3399.
13. For copper-catalyzed allylic alkylations in the presence of dialkylzinc reagents, see: a) F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391-393; Angew. Chem. Int. Ed. 1999, 38, 379-381; b) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460; c) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171; d) S. Ongeri, U. Piarulli, M. Roux, C. Monti, C. Gennari, Helv. Chim. Acta 2002, 3388-3399.
14. For copper-catalyzed allylic alkylations in the presence of dialkylzinc reagents, see: a) F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391-393; Angew. Chem. Int. Ed. 1999, 38, 379-381; b) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460; c) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171; d) S. Ongeri, U. Piarulli, M. Roux, C. Monti, C. Gennari, Helv. Chim. Acta 2002, 3388-3399.
15. For copper-catalyzed allylic alkylations in the presence of dialkylzinc reagents, see: a) F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391-393; Angew. Chem. Int. Ed. 1999, 38, 379-381; b) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508; Angew. Chem. Int. Ed. 2001, 40, 1456-1460; c) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171; d) S. Ongeri, U. Piarulli, M. Roux, C. Monti, C. Gennari, Helv. Chim. Acta 2002, 3388-3399.
16. a) I. Chataigner, C. Gennari, U. Piarulli, S. Ceccarelli, Angew. Chem. 2000, 112, 953-956; Angew. Chem. Int. Ed. 2000, 39, 916-918;
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21. 6, and in the absence of the chiral ligand gave only starting material and minute amounts of 3/4 (8%).
22. 3, c=1.2). The above synthetic sequence was also performed with MeMgCl and PhMgCl instead of EtMgCl, yielding enantiomerically pure (1S,2S)-5 (R =Me) and (1S,2R)-7 (R = Ph). See: a) M. Ito, M. G. Murugesh, Y. Kobayashi, Tetrahedron Lett. 2001, 42, 423-427; b) M. Ito, M. Matsuumi, M. G. Murugesh, Y. Kobayashi, J. Org. Chem. 2001, 66, 5881-5889; c) Y. Kobayashi, M. Ito, J. Igarashi, Tetrahedron Lett. 2002, 43, 4829-4832.
23. 3, c=1.2). The above synthetic sequence was also performed with MeMgCl and PhMgCl instead of EtMgCl, yielding enantiomerically pure (1S,2S)-5 (R =Me) and (1S,2R)-7 (R = Ph). See: a) M. Ito, M. G. Murugesh, Y. Kobayashi, Tetrahedron Lett. 2001, 42, 423-427; b) M. Ito, M. Matsuumi, M. G. Murugesh, Y. Kobayashi, J. Org. Chem. 2001, 66, 5881-5889; c) Y. Kobayashi, M. Ito, J. Igarashi, Tetrahedron Lett. 2002, 43, 4829-4832.
24. 3, c=1.2). The above synthetic sequence was also performed with MeMgCl and PhMgCl instead of EtMgCl, yielding enantiomerically pure (1S,2S)-5 (R =Me) and (1S,2R)-7 (R = Ph). See: a) M. Ito, M. G. Murugesh, Y. Kobayashi, Tetrahedron Lett. 2001, 42, 423-427; b) M. Ito, M. Matsuumi, M. G. Murugesh, Y. Kobayashi, J. Org. Chem. 2001, 66, 5881-5889; c) Y. Kobayashi, M. Ito, J. Igarashi, Tetrahedron Lett. 2002, 43, 4829-4832.
25. R: 26.2 min ((1R,2R)-6) and 26.7 min ((1S,2S)-5).
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30. 1H NMR spectroscopy; see: a) J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519; b) G. R. Sullivan, J. A. Dale, H. S. Mosher, J. Org. Chem. 1973, 38, 2143-2147.
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32. S conformation (plane symmetric), the cyclohexene derivative 9 (n=1) is better described as a mixture of readily interconverting enantiomers.