Enantioselective Synthesis of 1- and 4-Hydroxytetrahydrocarbazoles through Asymmetric Transfer Hydrogenation

Autor:	Erkan Ertürk, Ömer Dilek, Süleyman Patir
Rok vydání:	2018
Předmět:	chemistry.chemical_classification chemistry Hydrogen Yield (chemistry) Organic Chemistry Enantioselective synthesis Moiety Organic chemistry chemistry.chemical_element Enantiomer Transfer hydrogenation Lactone Catalysis
Zdroj:	Synlett. 30:69-72
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0037-1610351
Popis:	Several 1- and 4-hydroxytetrahydrocarbazoles were prepared in high yields (up to 99%) and excellent enantiomeric excesses (up to >99% ee) from the corresponding 1- and 4-oxotetrahydrocarbazoles through asymmetric transfer hydrogenation by using the commercially available Noyori–Ikariya ruthenium catalyst. The immediate use of the freshly prepared catalyst and the use of a HCO2H–DABCO (11:6) mixture as the hydrogen source are crucial for achieving high activity and enantioselectivity. In this way, a tetrahydrocarbazole heterocycle fused to a lactone moiety was synthesized in 45% yield and 97% ee.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f0e157a9812fd5d3f8bf6f07dab67678 https://doi.org/10.1055/s-0037-1610351 Zobrazit plný text záznamu