Zr(OBu(t))4 as a new promoter for the Meerwein-Ponndorf-Verley alkynylation and cyanation of aldehydes

Synlett

Volumn , Issue 1, 2000, Pages 69-70

  Ooi, Takashi ^a   Takaya, Keisuke ^a   Miura, Tomoya ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Acetone cyanohydrin; Aldehydes; Cyanation; Meerwein Ponndorf Verley alkynylation; Zirconium alkoxides

Indexed keywords

ALDEHYDE DERIVATIVE; ZIRCONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0033977504     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (11)

1. T. Ooi, T. Miura, and K. Maruoka, J. Am. Chem. Soc., 120, 10790 (1998).
2. 4 as a catalyst for Meerwein-Ponndorf-Verley reduction and Oppenauer oxidation, see: (a) B. Knauer and K. Krohn, Liebigs Ann., 677 (1995).
3. (b) B. Knauer and K. Krohn, Liebigs Ann., 1347 (1995).
4. (c) B. Knauer and K. Krohn, Recl. Trav. Chim. Pays-Bas, 115, 140 (1996).
5. (d) K. Krohn, B. Knauer, J. Kupke, D. Seebach, A. K. Beck, and M. Hayakawa, Synthesis, 1341 (1996).
6. For other synthetic applications: (a) H. Sasai, Y. Kirio, and M. Shibasaki, J. Org. Chem., 50, 5306 (1990).
7. (b) W. A. Nugent, J. Am. Chem. Soc., 114, 2768 (1992).
8. (c) H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 119, 7153 (1997).
9. (d) H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 120, 431 (1998).
10. (e) S. Kobayashi, S. Komiyama, and H. Ishitani, Angew. Chem. Int. Ed., 37, 979 (1998).
11. 2,2-Dichlorodecanal (3) was readily prepared from decanal according to the literature procedure. See: R. Verhe, N. De Kimpe, L. De Buyck, and N. Schamp, Synthesis, 455 (1975).