Asymmetric synthesis of (R,S)- and (R,R)-4-hydroxy-5-(α-Substituted)- hydroxymethyl[2.2]Paracyclophane and derivatives by stereoselective addition to (R)-4-hydroxy-5-formyl[2.2]paracyclophane and derivatives

Tetrahedron Asymmetry

Volumn 7, Issue 12, 1996, Pages 3445-3454

  Sergeeva, Elena V ^a   Rozenberg, Valeria I ^a   Vorontsov, Evgenii V ^a   Danilova, Tat'yana I ^a   Starikova, Zoya A ^a   Yanovsky, Alexandr I ^a   Belokon', Yuri N ^a   Hopf, Henning ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; PARACYCLOPHANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030561423     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00452-1     Document Type: Article

References (17)

1. 1. Eliel E. L., Willen S. H., Stereochemistry of Organic Compounds, Willey & Sons, New York, 1994.
2. 2. S. G. Davies, T. McCarthy, Transition metal arene complexes: side chain activation and conrol of stereochemistry. In: Comprehensive organometallic chemistry. E. W. Abel, F. Gordon A. Stone, G. Wilkinson, Pergamon, 1995, vol. 12, 1039-1070.
3. 3. A. Meyer, R. Dabard, J. Organomet. Chem., 1972, 36, C38-C42; S. Top, G. Jaouen, J. Org. Chem., 1981, 46, 78-82; M. Uemura, T. Kobayashi, T. Minami, Y. Hayashi, Tetrahedron Lett., 1986, 27, 2479-2482; A. Solladie-Cavallo, S. Quazzotti, S. Colonna, A. Manfredi, Tetrahedron Lett., 1989, 30, 2933-2936; S. G. Davies, C. L. Goodfellow, J. Chem. Soc. Perkin Trans. I, 1989, 192-194.
4. 3. A. Meyer, R. Dabard, J. Organomet. Chem., 1972, 36, C38-C42; S. Top, G. Jaouen, J. Org. Chem., 1981, 46, 78-82; M. Uemura, T. Kobayashi, T. Minami, Y. Hayashi, Tetrahedron Lett., 1986, 27, 2479-2482; A. Solladie-Cavallo, S. Quazzotti, S. Colonna, A. Manfredi, Tetrahedron Lett., 1989, 30, 2933-2936; S. G. Davies, C. L. Goodfellow, J. Chem. Soc. Perkin Trans. I, 1989, 192-194.
5. 3. A. Meyer, R. Dabard, J. Organomet. Chem., 1972, 36, C38-C42; S. Top, G. Jaouen, J. Org. Chem., 1981, 46, 78-82; M. Uemura, T. Kobayashi, T. Minami, Y. Hayashi, Tetrahedron Lett., 1986, 27, 2479-2482; A. Solladie-Cavallo, S. Quazzotti, S. Colonna, A. Manfredi, Tetrahedron Lett., 1989, 30, 2933-2936; S. G. Davies, C. L. Goodfellow, J. Chem. Soc. Perkin Trans. I, 1989, 192-194.
6. 3. A. Meyer, R. Dabard, J. Organomet. Chem., 1972, 36, C38-C42; S. Top, G. Jaouen, J. Org. Chem., 1981, 46, 78-82; M. Uemura, T. Kobayashi, T. Minami, Y. Hayashi, Tetrahedron Lett., 1986, 27, 2479-2482; A. Solladie-Cavallo, S. Quazzotti, S. Colonna, A. Manfredi, Tetrahedron Lett., 1989, 30, 2933-2936; S. G. Davies, C. L. Goodfellow, J. Chem. Soc. Perkin Trans. I, 1989, 192-194.
7. 3. A. Meyer, R. Dabard, J. Organomet. Chem., 1972, 36, C38-C42; S. Top, G. Jaouen, J. Org. Chem., 1981, 46, 78-82; M. Uemura, T. Kobayashi, T. Minami, Y. Hayashi, Tetrahedron Lett., 1986, 27, 2479-2482; A. Solladie-Cavallo, S. Quazzotti, S. Colonna, A. Manfredi, Tetrahedron Lett., 1989, 30, 2933-2936; S. G. Davies, C. L. Goodfellow, J. Chem. Soc. Perkin Trans. I, 1989, 192-194.
8. 4. M. Uemura, R. Miyake, K. Nakayama, M. Shiro, Y. Hayashi, J. Org. Chem., 1993, 58, 1238-1244 and references cited therein.
9. 5. H. J. Reich, K. E. Yelm, J. Org. Chem., 1991, 56, 5672-5679; A. Pelter, R. A. N. C. Crump, H. Kidwell, Tetrahedron Lett., 1996, 37, 1273-1276.
10. 5. H. J. Reich, K. E. Yelm, J. Org. Chem., 1991, 56, 5672-5679; A. Pelter, R. A. N. C. Crump, H. Kidwell, Tetrahedron Lett., 1996, 37, 1273-1276.
11. 1, Angew. Chem., 1994, 106, 106-108, Angew. Chem. Int. Ed Ingl., 1994, 33, 91-92.
12. 1, Angew. Chem., 1994, 106, 106-108, Angew. Chem. Int. Ed Ingl., 1994, 33, 91-92.
13. 7. H. Hopf, D. G. Barrett, Liebigs Ann., 1995, 449-452.
14. 1, N. S. Ikonnikov, S. A. Orlova, A. P. Pisarevsky, N. I. Raevsky, V. I. Rozenberg, E. V. Sergeeva, Yu. T. Struchkov, V. I. Tararov, E. V. Vorontsov, J. Chem. Soc., Perkin Trans. I, 1995, 1873-1879.
15. 9. The hydroxy hydrogen atom is involved in the intramolecular H-bond O(1)-H(1)...O(2) (O...O 2.702(5) O-H 0.80(4), H...O 1.97(4)Å, O-H...O 149(4)°), which closes the six-membered H-bonded cycle, fused to one of the paracyclophane aromatic rings.
16. 10. M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans. I, 1992, 3135-3140.
17. 11. The same number of mmol of (R)-FHPC, (R)-2, (R)-3 and Grignard reagents were used in each experiment. Reaction of 0.054 g (0.21 mmol) of (R)-FHPC was carried out with 0.59 ml of 0.88N n-BuLi solution in hexane (0.52 mmol). (R,R)-12 was obtained from 0.084 g (0.26 mmol) of (R)-4 and 0.58 ml of 1N EtMgI solution (0.58 mmol).