Simultaneous functional group manipulation in the Meerwein-Ponndorf- Verley reduction process catalyzed by bidentate aluminum reagent

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2137-2138

  Ooi, Takashi ^a   Itagaki, Yoshifumi ^a   Miura, Tomoya ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; CARBONYL DERIVATIVE; HYDROXYL GROUP; REAGENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033548473     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00131-8     Document Type: Article

References (6)

1. Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989.
2. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 2347 and references cited therein.
3. (a) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
4. (b) Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403.
5. (c) Ooi, T.; Takahashi, M.; Maruoka, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 835.
6. ;2; at 21 °C for 2 h resulted in 77% recovery of the hydroxy ketone with concomitant formation of 4-(2-hydroxypropyl)cyclohexan-1-one (the starting material in entries 3-5), 4-(2-oxopropyl)cyclohexan-1-one and 4-(2-hydroxypropyl)cyclohexane-1-ol in <1%, 12% and 10% yields, respectively.