Reductive Cleavage of Acetals and Ketals with 9-Borabicyclo[3.3.1]nonane

Autor:	and Iveliz Kock, John A. Soderquist, Maria E. Estrella
Rok vydání:	2006
Předmět:	Benzaldehyde chemistry.chemical_compound Chemistry Dimer Organic Chemistry Moiety Organic chemistry Ether Physical and Theoretical Chemistry Nonane 9-Borabicyclo[3.3.1]nonane Acetophenone Styrene
Zdroj:	Organic Process Research & Development. 10:1076-1079
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op0601262
Popis:	The reductive cleavage of benzaldehyde acetals and acetophenone ketals with the air-stable crystalline 9-borabicyclo[3.3.1]nonane dimer provides monobenzylated ether derivatives of diols and 1,2-oxygen-transposed β-phenethyl alcohols, respectively. The boron moiety is effectively recovered through simple procedures which involve convenient air-stable reagents and boron byproducts. The process is particularly selective for 1,3-diols giving the more substituted monobenzyl ether derivatives exclusively. With acetophenone ketals both reduction and elimination occur, permitting 9-BBN-H to hydroborate the resulting styrene to produce 1,2-oxygen-transposed β-phenethyl alcohols cleanly. Potential applications of this new process were illustrated with the synthesis of the hallucinogen, mescaline, and the analgesic, ibufenac.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::66e3e43fcdcf8284d5815105bd78d75c https://doi.org/10.1021/op0601262 Zobrazit plný text záznamu