Selective reduction of organic compounds with Al-acetoxy- and Al-trifluoroacetoxydiisobutylalane

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 65, Issue 1, 2009, Pages 15-23

  Cha, Jin Soon ^a   Yi, Ja Eun ^a  

^a Yeungnam University   (South Korea)

Author keywords

Al acetoxydiisobutylalane; Al trifluoroacetoxydiisobutylalane; Organic functional groups; Selective reduction; Stereoreduction

Indexed keywords

EID: 76349125993     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9629-3     Document Type: Article

References (14)

1. Cha, J. S., Nam, H. T., Park, S. J., Kwon, S. Y., Kwon, O. O.: Selective reduction of carbonyl compounds with B-acetoxy- and B-trifluoroacetoxydiisopinocampheylboranes. Bull. Korean Chem. Soc 27, 667-671 (2006).
2. Cohen, R., Graves, C. R., Nguyew, S. T., Martin, J. M. L., Ratner, M. A.: The mechanism of aluminum-catalyzed Meerwein-Schmidt-Ponndorf-Verley reduction of carbonyls to alcohols. J. Am. Chem. Soc. 126, 14796-14803 (2004).
3. Cha, J. S., Kwon, O. O., Kwon, S. Y., Kim, J. M., Seo, W. W., Chang, S. W.: Chemoselective reduction of carbonyl compounds with diisobutylchloroalane. Synlett 1055-1056, 1995.
4. Cha, J. S., Kown, O. O., Kwon, S. Y.: Selective reduction of α,β-unsaturated aldehydes and ketones to allylic alcohols with diisobutylchloroalane. Bull. Korean Chem. Soc. 16, 1009-1011 (1995).
5. Cha, J. S., Kwon, O. O., Kwon, S. Y.: Selective reduction of α,β-unsaturated aldehydes and ketones to allylic alcohols with diisobutylalkoxyalanes. Org. Prep. Proced. Int. 28, 355-359 (1996).
6. Cha, J. S., Kown, S. Y., Kwon, O. O., Kim, J. M.: Selective reduction of carbonyl compounds with diisobutyldialkylaminoalanes. Bull. Korean Chem. Soc. 17, 900-905 (1996).
7. Cha, J. S., Kwon, O. O.: Al-isopropoxydiisobutylalane. A stereoselective reducing agent for reduction of cyclic ketones to thermodynamically more stable alcohols. J. Org. Chem. 62, 3019-3020 (1997).
8. Cha, J. S., Kwon, O. O.: Reexamination of Al-isopropoxydiisobutylalane as a stereoselective reducing agent for reduction of cyclic ketones to thermodynamically more stable alcohols. Bull. Korean Chem. Soc 18, 689-690 (1997).
9. Cha, J. S., Kwon, O. O., Kim, J. M., Chun, J. H., Lee, Y. S., Lee, H. S., Cho, S. D.: Selective reduction of carbonyl compounds with Al-alkoxydiisobutylalanes. Bull. Korean Chem. Soc. 19, 236-242 (1998).
10. Kwon, O. O., Cha, J. S.: l-pyrrolyldiisobutylalane. A stereoselective reducing agent for reduction of cyclic ketones to thermodynamically more stable alcohols. Bull. Korean Chem. Soc. 21, 659-661 (2000).
11. Cha, J. S.: Recent developments in Meerwein-Ponndorf-Verley and related reactions for the reduction of organic functional groups using aluminum, boron, and other metal reagents: a review. Org. Process Res. Dev. 10, 1032-1053 (2006).
12. Cha, J. S.: Selective reduction of carbonyl and epoxy compounds using aluminum, boron and other metal reagents. Comparison of reducing characteristics between the Meerwein-Ponndorf-Verley type reduction and metal complex hydrides reduction: a review. Bull. Korean Chem. Soc. 28, 2162-2190 (2007).
13. Cha, J. S., Park, J. H.: Reaction of epoxides with boron triisopropoxide. The Meerwein-Ponndorf-Verley type reduction of boron alkoxides. Bull. Korean Chem. Soc. 23, 1377-1378 (2002).
14. Cha, J. S., Park, S. J., Yu, S. J., Kim, S. K., Kwon, O. O.: Regioselective cleavage of phenyl- or alkyl-substituted epoxides with Al-fluorodiisobutylalane. Bull. Korean Chem. Soc. 29, 301-302 (2008).