Stereoselective dihydroxylation of 2-alkyl- and 2,4-dialkyl-2-amido-3- cyclohexen-1-ones. Synthesis of enantiomerically related 2-alkyl- and 2,4- dialkyl-3-hydroxy-1-oxocyclohexan-2,4-carbolactones by complementary butyrolactonization reactions

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6663-6666

  Schultz, Arthur G ^a   Dai, Mingshi ^a   Tham, Fook S ^a   Zhang, Xuqing ^a  

^a RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

Asymmetric Synthesis; Epimerization; Hydroxylation; Lactonization

Indexed keywords

2 AMIDO 3 CYCLOHEXEN 1 ONE DERIVATIVE; 3 HYDROXY 1 OXOCYCLOHEXAN 2,4 CARBOLACTONE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ESTERIFICATION; HYDROGEN BOND; HYDROGENATION; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0032505232     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01440-3     Document Type: Article

References (16)

1. 1. (a) Schultz, A. G. Acc. Chem. Res. 1990, 23, 207-213.
2. (b) Schultz, A. G. J. Chinese Chem. Soc. (Taiwan) 1994, 41, 487-495.
3. 2. Crabtree, R. H.; Felkin, H.; Fellebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 168, 183-195.
4. 3. (a) Schultz, A. G.; McCloskey, P. J. J. Org. Chem. 1985, 50, 5905-5907.
5. (b) McCloskey, P. J.; Schultz, A. G. Heterocycles 1987, 25, 437-447.
6. (c) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502.
7. (d) Schultz, A. G.; Green, N. J. J. Am. Chem. Soc. 1991, 113, 4931-4936.
8. (e) Schultz, A. G.; Hoglen, D. K.; Holoboski, M. A. Tetrahedron Lett. 1992, 33, 6611-6614.
9. 4. Schultz, A. G.; Harrington, R. E.; Tham, F. S. Tetrahedron Lett. 1992, 33, 6097-6100.
10. 4-TMEDA reagent, see: Donohoe, T. J.; Moore, P. R.; Waring, M. J. Tetrahedron Lett. 1997, 38, 5027-5030. See references in this paper for other examples of the directed dihydroxylation of alkenes.
11. 6. Hauser, F. M.; Ellenberger, S. R.; Clardy, J. C.; Bass, L. S. J. Am. Chem. Soc. 1984, 106, 2458-2459.
12. 7. For the preparation of 2a-2f, see: Schultz, A. G.; Dai, M.; Khim, S.-K.; Pettus, L.; Thakkar, K. Tetrahedron Lett. 1998, 39, 4203.
13. 5: C, 67.84; H, 8.02. Found: C, 67.72; H, 8.07.
14. 9. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271-1275 and references cited therein.
15. 3).
16. 2H reference): 5d, δ 4.70; 8d, 4.35; 5f, 4.70; 8f, 4.56.