A new lithium alkoxide accelerated diastereoselective cyanation of ketones

Autor:	Stephen A. Wald, C H Senanayake, R P Bakale, Charles P. Vandenbossche, Harold Scott Wilkinson, Nandkumar N. Bhongle, Paul Grover
Rok vydání:	2001
Předmět:	High rate Organic Chemistry Heteroatom chemistry.chemical_element Alcohol Cyanation Biochemistry Fenchone chemistry.chemical_compound chemistry Yield (chemistry) Alkoxide Organic chemistry Lithium Physical and Theoretical Chemistry
Zdroj:	Organic letters. 3(4)
ISSN:	1523-7060
Popis:	[reaction: see text] A remarkably general lithium heteroatom assisted TMSCN or TBSCN addition to aldehydes and ketones has been discovered. The process provides excellent selectivities and high rates. Conformationally constrained ketones such as camphor, fenchone, and nopinone give excellent diastereoselectivities with TMSCN. Reduction of 2 provided diastereopure amino alcohol 3 in good yield. alpha- and beta-Methyl cyclohexanones with TBSCN-LiOR afford high diastereoselectivities and yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::03a34d06e5b891b5f0f03c73b5e77c90 https://pubmed.ncbi.nlm.nih.gov/11178823 Zobrazit plný text záznamu