Redox isomerization of allylic alcohols and amides using Grubbs' catalyst

Synthetic Communications

Volumn 33, Issue 2, 2003, Pages 223-228

  Greenwood, E S ^a   Parsons, P J ^a   Young, M J ^b  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Allylic alcohol; Allylic amide; Grubbs' catalyst; Redox isomerization

Indexed keywords

ALLYL ALCOHOL; AMIDE;

ARTICLE; CATALYSIS; CATALYST; IONIZATION; ISOMERISM; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; RING CLOSING METATHESIS;

EID: 0037272918     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015704     Document Type: Article

References (8)

1. For recent reviews on olefin metathesis see: (a) Schuster, M.; Blechart, S. Olefin metathesis in organic chemistry. Angew. Chem. Int. Ed. (Engl.) 1997, 36 (19), 2037-2056; (b) Grubbs, R.H.; Chang, S. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 1998, 54 (18), 4413-4450; (c) Armstrong, S.K. Ring closing diene metathesis in organic synthesis. J. Chem. Soc., Perkin I 1998, (2), 371-388.
2. For recent reviews on olefin metathesis see: (a) Schuster, M.; Blechart, S. Olefin metathesis in organic chemistry. Angew. Chem. Int. Ed. (Engl.) 1997, 36 (19), 2037-2056; (b) Grubbs, R.H.; Chang, S. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 1998, 54 (18), 4413-4450; (c) Armstrong, S.K. Ring closing diene metathesis in organic synthesis. J. Chem. Soc., Perkin I 1998, (2), 371-388.
3. For recent reviews on olefin metathesis see: (a) Schuster, M.; Blechart, S. Olefin metathesis in organic chemistry. Angew. Chem. Int. Ed. (Engl.) 1997, 36 (19), 2037-2056; (b) Grubbs, R.H.; Chang, S. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 1998, 54 (18), 4413-4450; (c) Armstrong, S.K. Ring closing diene metathesis in organic synthesis. J. Chem. Soc., Perkin I 1998, (2), 371-388.
4. (a) Trost, B.M.; Kulawiec, R.J. A chemoselective internal redox of allyl alcohols to saturated aldehydes or ketones. Tetrahedron Lett. 1991, 32 (26), 3039-3042;
5. (b) Trost, B.M.; Kulawiec, R.J. Chemoselectivity in the ruthenium-catalyzed redox isomerization of allyl alcohols. J. Am. Chem. Soc. 1993, 115 (5), 2027-2036.
6. Bäckvall, J.-E.; Andreasson, U. Ruthenium-catalyzed isomerization of allylic alcohols to saturated ketones. Tetrahedron Lett. 1993, 34 (34), 5459-5462.
7. Nakashima, K.; Ito, R.; Sono, M.; Tori, M. Olefin metathesis reactions of some aromatic dienes with ortho- and meta-disubstitution, formation of 10-, 12-, 14-, and 17-membered cyclic compounds and isomerization of an allylic alcohol. Heterocycles 2000, 53 (2), 301.
8. +. J. Organomet. Chem. 1990, 395 (2), C39-C41.