Effect of solvent and lithiating agent on stereoselectivity in lithiation of chiral 1,1'-bis(oxazolinyl)ferrocenes

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6137-6140

  Park, Jaiwook ^a   Lee, Sunwoo ^a   Ahn, Kyo Han ^a   Cho, Chang Woo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BIS(OXAZOLINYL)FERROCENE DERIVATIVE; ALCOHOL; FERROCENE DERIVATIVE; LITHIUM DERIVATIVE; SOLVENT; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; PHOSPHORYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0030593610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01331-7     Document Type: Article

References (13)

1. 1. Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180-186 and references therein.
2. 2. For leading references, see: Ferrocenes; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, 1995.
3. 3. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11 and references therein.
4. 4. Park, J.; Lee, S.; Ahn, K. H.; Cho, C. W. Tetrahedron Lett. 1995, 36, 7263-7265.
5. 5. The configurations of (R)-2 and (R,R)-3 have been assigned to the opposite direction in the previous paper: See ref. 4.
6. w = 0.045, G.O.F. = 0.48. Atomic coordinates, bond lengths, angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Center.
7. 3): δ 164.8, 164.4, 140.2, 140.0, 138.7, 138.5, 135.7, 135.5, 133.2, 133.0, 129.6, 128.9, 128.8, 128.7, 128.6, 128.5, 81.0, 80.9, 76.8, 75.4, 74.8, 74.5, 74.3, 73.4, 73.1, 71.9, 71.4, 69.1, 69.0, 34.1 34.0, 26.6, 26.4.
8. 8. At -78°C 1.0 equiv of s-BuLi was added. The reaction mixture was stirred for 2 h at -78°C and was warmed up slowly to 25°C over 1 h. Then additional 1.2 equiv of S-BuLi was added dropwise.
9. 9. Ikeda group has reported the diastereoselective preparation of (S,S)-3 by use of S-BuLi (2.6 equiv) in THF, see: Zhang, W.; Adachi, Y.; Hirao, T.; Ikeda, I. Tetrahedron: Asymmetry, 1996, 7, 451-460.
10. 10. a) Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74-76.
11. b) Nishibashi, Y.; Uemura, S. Synlett 1995, 79-81.
12. 11. a) Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629-1635.
13. b) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003.