Mild preparation of allylic tartaramide acetals in DMF

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7197-7200

  Molander, Gary A ^a   McWilliams, J Christopher ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TARTARIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030607203     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01637-1     Document Type: Article

References (21)

1. 1. For a review, see: (a) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
2. For more recent work in this field, see: (b) Sammakia, T.; Smith, R.S. J. Am. Chem. Soc. 1992, 114, 10998, and references cited therein.
3. (c) Aubé, J.; Heppert, J.A.; Milligan, M.L.; Smith, M.J.; Zenk, P. J. Org. Chem. 1992, 57, 3563.
4. (d) Parrain, J.-L.; Cintrat, J.-C.; Qintard, J.-P. J. Organomet. Chem. 1992, 437, C19.
5. (e) Longobardo, L.; Mobbili, G.; Tagliavini, T.; Trombini, C.; Umani-Ronchi, A. Tetrahedron 1992, 48, 1299.
6. (f) Yuan, R.-M.; Yea, S.-M.; Hsieh, Y.-T.; Luh, T.-Y. J. Org. Chem. 1994, 59, 8192.
7. (g) For a recent example of the application of chiral acetals to asymmetric cyclopropanations, see: Armstrong, R.W.; Maurer, K.W. Tetrahedron Lett. 1995, 36, 357.
8. 2. (a) Molander, G.A.; McWilliams, J.C. manuscript submitted.
9. (b) Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986.
10. See also: (c) Reference 1a.
11. (d) Maruoka, K.; Nakai, S.; Saturai, M.; Yamamoto, H. Synthesis 1986, 130.
12. (e) Fujiwara, J.; Fukulani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004.
13. (f) Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1984, 25, 5911.
14. 3. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis; 2nd ed.; John Wiley & Sons, Inc.: New York, 1991.
15. 4. (a) Hwu, J.R.; Leu, L-C.; Robl, J.; Anderson, D.A.; Wetzel, J.M. J. Org. Chem. 1987, 52, 188.
16. (b) Tsunoda, R.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
17. 5. At lower temperatures, only epimeric mixtures of the mixed acetals 27 were formed. (equation presented)
18. 3, which hydrolyzed 7 to the diol 3. The diol 3 could then be readily washed from the product.
19. 7. It was assumed that the rate-determining step was the formation of a charged transition state (i.e. an oxocarbenium ion) from an uncharged species.
20. 4) and concentration, the crude was purified by silica gel chromatography (92:8 EtOAc/MeOH), yielding 15 (98:2 E/Z, 883 mg, 79%).
21. 9. Small amounts of products in which both the aldehyde and ketone functionalities were acetalated with the tartaramide diol could have gone undetected by GC due to their high boiling points. This material would have washed out during workup.