Enantioselective Alkynylation Reactions to Substituted Benzaldehyde and Salicylaldehyde Derivatives: The Effect of Substituents upon the Efficiency and Enantioselectivity

Autor:	Alastair Mann, Elizabeth Tyrrell, Kuldip Singh, Kibur Hunie Tesfa
Rok vydání:	2007
Předmět:	Chemistry Organic Chemistry Enantioselective synthesis Nicholas reaction General Medicine Ring (chemistry) Medicinal chemistry Catalysis Benzaldehyde chemistry.chemical_compound Phenylacetylene Alkynylation Salicylaldehyde Yield (chemistry) Organic chemistry N-Methylephedrine
Zdroj:	ChemInform. 38
ISSN:	1522-2667 0931-7597
Popis:	Asymmetric alkynylation reactions to mono-, di-, and trisubstituted aromatic aldehydes have been accomplished in good yields and with a range of selectivities. For salicylaldehyde derivatives both the yield and the enantioselectivity of the alkynylation reaction appears to depend not only upon the electron-donating/ electron-withdrawing nature of substituents but also upon their position in the ring relative to the carbonyl. For benzaldehyde derivatives this observation is exemplified with nitrobenzaldehyde wherein asymmetric alkynylation with 3-nitrobenzaldehyde occurs in virtually quantitative yield and enantioselectivity. In contrast our attempts at asymmetric alkynylations with 4-nitrobenzaldehyde failed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b02b18d3e32c395a27ccbdcf32c4288d https://doi.org/10.1002/chin.200739079 Zobrazit plný text záznamu Plný text