Solid phase aldol and conjugate addition reactions using Evans' oxazolidinone chiral auxiliary

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2655-2658

  Phoon, Chee Wee ^a   Abell, Chris ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE; RESIN;

ARTICLE; CHIRALITY; CONJUGATE; ENANTIOMER; REACTION ANALYSIS;

EID: 0032560075     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00230-5     Document Type: Article

References (23)

1. 1. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; ibid. 1997, 53, 5643-5678.
2. 1. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554; ibid. 1997, 53, 5643-5678.
3. 2. Examples include: Kawana, M.; Emoto, S. Tetrahedron Lett., 1972, 4855-4858; Worster, P. M.; Mc Arthur, C. R.; Leznoff, C. C. Angew. Chem. Int. Ed. Engl., 1979, 3, 221-222; Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem., 1981, 46, 3097-3102; Moon, H-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem., 1992, 57, 6088-6089; Moon, H-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 8915-8918; Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett., 1996, 8023-8026.
4. 2. Examples include: Kawana, M.; Emoto, S. Tetrahedron Lett., 1972, 4855-4858; Worster, P. M.; Mc Arthur, C. R.; Leznoff, C. C. Angew. Chem. Int. Ed. Engl., 1979, 3, 221-222; Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem., 1981, 46, 3097-3102; Moon, H-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem., 1992, 57, 6088-6089; Moon, H-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 8915-8918; Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett., 1996, 8023-8026.
5. 2. Examples include: Kawana, M.; Emoto, S. Tetrahedron Lett., 1972, 4855-4858; Worster, P. M.; Mc Arthur, C. R.; Leznoff, C. C. Angew. Chem. Int. Ed. Engl., 1979, 3, 221-222; Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem., 1981, 46, 3097-3102; Moon, H-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem., 1992, 57, 6088-6089; Moon, H-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 8915-8918; Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett., 1996, 8023-8026.
6. 2. Examples include: Kawana, M.; Emoto, S. Tetrahedron Lett., 1972, 4855-4858; Worster, P. M.; Mc Arthur, C. R.; Leznoff, C. C. Angew. Chem. Int. Ed. Engl., 1979, 3, 221-222; Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem., 1981, 46, 3097-3102; Moon, H-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem., 1992, 57, 6088-6089; Moon, H-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 8915-8918; Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett., 1996, 8023-8026.
7. 2. Examples include: Kawana, M.; Emoto, S. Tetrahedron Lett., 1972, 4855-4858; Worster, P. M.; Mc Arthur, C. R.; Leznoff, C. C. Angew. Chem. Int. Ed. Engl., 1979, 3, 221-222; Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem., 1981, 46, 3097-3102; Moon, H-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem., 1992, 57, 6088-6089; Moon, H-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 8915-8918; Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett., 1996, 8023-8026.
8. 2. Examples include: Kawana, M.; Emoto, S. Tetrahedron Lett., 1972, 4855-4858; Worster, P. M.; Mc Arthur, C. R.; Leznoff, C. C. Angew. Chem. Int. Ed. Engl., 1979, 3, 221-222; Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem., 1981, 46, 3097-3102; Moon, H-S.; Schore, N. E.; Kurth, M. J. J. Org. Chem., 1992, 57, 6088-6089; Moon, H-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 8915-8918; Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett., 1996, 8023-8026.
9. 3. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichchimica Acta 1997, 30, 3-12.
10. 4. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 83-91.
11. 5. Evans, D. A.; Bilodeau, M. T.; Somers, T. C.; Clardy, J.; Cherry, D.; Kato, Y. J. Org. Chem. 1991, 56, 5750-5752.
12. 6. Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 6851-6852.
13. 7. Burgess, K.; Lim, D. J. Chem. Soc. Chem. Commun. 1997, 785-786.
14. 8. Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 8777-8780.
15. 9. Gage, J. R.; Evans, D. A.Org. Synth. 1990,68, 77-82.
16. 10. The loading capacites of hydroxymethyl polystyrene resin used were 0.79 mmol/g for the aldol reaction, 1.49 mmol/g for the Michael addition. The attachment of the chiral auxiliary was quantitative as determined by nitrogen analysis.
17. 11. The chiral auxiliary was also attached to Wang resin. However under the Lewis acidic conditions used for the aldol reaction (enolisation with n-dibutylboron triflate and triethylamine), partial cleavage of the auxiliary from the resin was observed. This was not a problem with the auxiliary attached to hydroxymethyl resin 5.
18. 12. Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem., 1990, 55, 173-181.
19. 13. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 6141-6144
20. 14. Vedejs, E.; Gingras, M. J. Am. Chem. Soc., 1994, 116, 579-588.
21. 15. Examples include: Ley, S. V.; Mynett, D. M.; Koot, W.-J. Synlett. 1995, 1017-1020; Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 6473-6476.
22. 15. Examples include: Ley, S. V.; Mynett, D. M.; Koot, W.-J. Synlett. 1995, 1017-1020; Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 6473-6476.
23. 16. A conjugate addition reaction using ethyl vinyl ketone precomplexed with titanium tetrachloride as the Michael acceptor was unsuccessful. The insolubility of the titanium complex in dichloromethane prevented it penetrating the resin.