Grignard additions to α,β-unsaturated dioxolanones: Preparation of chiral allylic alcohols and protected α-hydroxy aldehydes

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1421-1424

  Heckmann, B ^a   Mioskowski, C ^a   Bhatt, Rama K ^b   Falck, J R ^b  

^a CNRS   (France)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ESTER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029933371     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00058-5     Document Type: Article

References (11)

1. Seebach, D.; Imwinkelried, R.; Stucky, G. Angew. Chem. Int. Ed. 1986, 25, 178-180. Mashraqui, S.H.; Kellogg, R.M. J. Org. Chem. 1984, 49, 2513-2516. Schreiber, S.L.; Reagan, J. Tetrahedron Lett. 1986, 27, 2945-2948.
2. Seebach, D.; Imwinkelried, R.; Stucky, G. Angew. Chem. Int. Ed. 1986, 25, 178-180. Mashraqui, S.H.; Kellogg, R.M. J. Org. Chem. 1984, 49, 2513-2516. Schreiber, S.L.; Reagan, J. Tetrahedron Lett. 1986, 27, 2945-2948.
3. Seebach, D.; Imwinkelried, R.; Stucky, G. Angew. Chem. Int. Ed. 1986, 25, 178-180. Mashraqui, S.H.; Kellogg, R.M. J. Org. Chem. 1984, 49, 2513-2516. Schreiber, S.L.; Reagan, J. Tetrahedron Lett. 1986, 27, 2945-2948.
4. Heckmann, B.; Mioskowski, C.; Yu, J.; Falck, J.R. Tetrahedron Lett. 1992, 33, 5201-5204.
5. Faunce, J.A.; Friebe, T.L.; Grisso, B.A.; Losey, E.N.; Sabat, M.; Mackenzie, P.B. J. Am. Chem. Soc. 1989, 111, 4508-4510. Krysan, D.J.; Mackenzie, P.B. ibid. 1988, 110, 6273-6274.
6. Faunce, J.A.; Friebe, T.L.; Grisso, B.A.; Losey, E.N.; Sabat, M.; Mackenzie, P.B. J. Am. Chem. Soc. 1989, 111, 4508-4510. Krysan, D.J.; Mackenzie, P.B. ibid. 1988, 110, 6273-6274.
7. Farines, M.; Soulier, J. Bull. Soc. Chim. Fr. 1970, 332-340.
8. 2O showed a dynamic equilibrium in which cis-1 was favored, e.g., cis/trans 64:36 at 18°C and 79:21 at -40°C.
9. 13C, and mass spectroscopy using chromatographically homogeneous samples.
10. Heckmann, B.; Alayrac, C.; Mioskowski, C.; Chandrasekhar, S.; Falck, J.R. Tetrahedron Lett. 1992, 33, 5205-5208.
11. Mosher esters of allylic alcohols 9 (R= Bu, iPr, Ph and hexynyl) schowed one single isomer.