Asymmetric synthesis of highly substituted β-lactones by nucleophile-catalyzed [2+2] cycloadditions of disubstituted ketenes with aldehydes

Angewandte Chemie - International Edition

Volumn 43, Issue 46, 2004, Pages 6358-6360

  Wilson, Jonathan E ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Aldehydes; Asymmetric catalysis; Cycloaddition; Ketenes; Lactones

Indexed keywords

ALDEHYDES; CATALYSTS; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE CYCLOADDITIONS; LACTONES;

KETONES;

ALDEHYDE DERIVATIVE; KETENE DERIVATIVE; LACTONE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL BOND; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; SYNTHESIS;

ALDEHYDES; CATALYSIS; CYCLIZATION; ETHYLENES; KETONES; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 11144311055     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460698     Document Type: Article

References (43)

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14. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
15. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
16. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
17. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
18. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
19. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
20. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
21. For chiral nucleophilic catalysts, see: a) D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1245-1251; D. Borrmann, R. Wegler, Chem. Ber. 1966, 99, 1575-1579; b) H. Wynberg, E. G. J. Staring, J. Am. Chem. Soc. 1982, 104, 166-168; H. Wynberg, E. G. J. Staring, J. Org. Chem. 1985, 50, 1977-1979; P. E. F. Ketelaar, H. Wynberg, E. G. J. Staring, Tetrahedron Lett. 1985, 26, 4665-4668; c) R. Tennyson, D. Romo, J. Org. Chem. 2000, 65, 7248-7252; G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731-1736; d) C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353.
22. Chiral Lewis acid catalysts: a) for an overview, see: ref. [8]; b) for leading references, see: S. G. Nelson, C. Zhu, X. Shen, J. Am. Chem. Soc. 2004, 126, 14-15.
23. Chiral Lewis acid catalysts: a) for an overview, see: ref. [8]; b) for leading references, see: S. G. Nelson, C. Zhu, X. Shen, J. Am. Chem. Soc. 2004, 126, 14-15.
24. Salinosporamide A and omuralide are two examples of natural products that include an α,α-disubstituted β-lactone. For leading references, see: L. R. Reddy, P. Saravanan, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 6230-6231.
25. a) For an early overview, see : G. C. Fu, Acc. Chem. Res. 2000, 33, 412-420;
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27. b) For more recent reports, see: A. H. Mermerian, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 4050-4051; I. D. Hills, G. C. Fu, Angew. Chem. 2003, 115, 4051-4054; Angew. Chem. Int. Ed. 2003, 42, 3921-3924.
28. b) For more recent reports, see: A. H. Mermerian, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 4050-4051; I. D. Hills, G. C. Fu, Angew. Chem. 2003, 115, 4051-4054; Angew. Chem. Int. Ed. 2003, 42, 3921-3924.
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31. See ref. [11b]. Examples of cinchona alkaloid-based intramolecular reactions of monosubstituted ketenes had been described earlier (ref. [10c]).
32. For reviews of catalytic asymmetric methods that generate quaternary stereocenters, see: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597; see also: I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10 105-10 146.
33. For reviews of catalytic asymmetric methods that generate quaternary stereocenters, see: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597; see also: I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10 105-10 146.
34. For reviews of catalytic asymmetric methods that generate quaternary stereocenters, see: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597; see also: I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10 105-10 146.
35. For reviews of catalytic asymmetric methods that generate quaternary stereocenters, see: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597; see also: I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10 105-10 146.
36. For reviews of catalytic asymmetric methods that generate quaternary stereocenters, see: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597; see also: I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10 105-10 146.
37. Notes: a) Under our standard conditions (Table 2), aryl alkyl ketenes, monosubstituted ketenes, very electron-rich aldehydes, and non-aromatic aldehydes are not suitable substrates. b) At the end of a reaction, we can typically recover about 80 % of catalyst 1.
38. A. Griesbeck, D. Seebach, Helv. Chim. Acta 1987, 70, 1326-1332. For a more recent study, see: S. G. Nelson, K. L. Spencer, Angew. Chem. 2000, 112, 1379-1381; Angew. Chem. Int. Ed. 2000, 39, 1323-1325.
39. A. Griesbeck, D. Seebach, Helv. Chim. Acta 1987, 70, 1326-1332. For a more recent study, see: S. G. Nelson, K. L. Spencer, Angew. Chem. 2000, 112, 1379-1381; Angew. Chem. Int. Ed. 2000, 39, 1323-1325.
40. A. Griesbeck, D. Seebach, Helv. Chim. Acta 1987, 70, 1326-1332. For a more recent study, see: S. G. Nelson, K. L. Spencer, Angew. Chem. 2000, 112, 1379-1381; Angew. Chem. Int. Ed. 2000, 39, 1323-1325.
41. For a review of the enantioselective synthesis of β-amino acids, see: a) E. Juaristi, Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York, 1997; b) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035.
42. For a review of the enantioselective synthesis of β-amino acids, see: a) E. Juaristi, Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York, 1997; b) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035.
43. 2NLi.