Ring closing metathesis of sterically hindered 1,6 - dienes: A new approach to 5-membered branched cyclitols

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5859-5860

  Sellier, Odile ^a   Van De Weghe, Pierre ^a   Eustache, Jacques ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; AMINOCYCLITOL;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033529802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01141-7     Document Type: Article

References (11)

1. Ovaa, H.; Codée, J.d.c.; Lastdrager, B.; Overkleeft, H.S.; van der Marel, G.A.; van Boom, J.H. Tetrahedron Lett. 1998, 39, 7987-7990.
2. Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853-856.
3. Kornienko, A.; d'Alarcao, M. Tetrahedron : Asymmetry 1999, 10, 827-829.
4. Picquet, M.; Bruneau, C.; Dixneuf, P.H. J.Chem.Soc., Chem. Commun. 1998, 2249-2250.
5. Holt, D.J.; Barker, W.D.; Jenkins, P.R.; Davies, D.L.; Garrat, S.; Fawcett, J.; Russell, D.R.; Ghosh, S. Angew. Chem. Int. Ed. 1998, 37, 3298-3300.
6. Both catalysts are available from STREM.
7. Similar results have been reported very recently. Kapferer, P.; Sarabia, F.; Vasella, A. Helv.Chim.Acta 1999, 82, 645-656. These authors describe the succesfull RCM of a sterically hindered 1,7-diene, using Grubb's catalyst, to afford valienamine.
8. The different behaviour of allylmagnesium bromide as compared to other Grignards when reacting with ketones bearing α chelating groups has been already noted. Alberto Marco, J.; Carda, M.; González, F.; Rodríguez, S.; Castillo, E.; Murga, J. J.Org.Chem. 1998, 63, 698-707.
9. For good results, utmost care should be used when working with the Schrock's catalyst. We use the following precautions : all manipulations were carried out under Ar, using glove box techniques. Freshly purchased catalyst is divided in small (10 mg) portions and then stored in vials, under Ar athmosphere, at -20°C. See also: Calimente, D.; Postema, M.H.D. J.Org.Chem. 1999, 64, 1770-1771.
10. 3, 62.9MHz) δ 2.23, 71.59, 72.20, 73.37, 76.06, 83.97, 84.20, 88.29, 127.35-128.33, 133.59, 136.42, 138-140.
11. Storch de Gracia, I.; Dietrich, H.; Bobo, S.; Chiara, J.L. J.Org.Chem. 1998, 63, 5883-5889.