Asymmetric synthesis of γ-chiral borylalkanes via sequential reduction/hydroboration using a single copper catalyst

Autor:	Jung Tae Han, Jaesook Yun, Jin Yong Lee
Rok vydání:	2020
Předmět:	Chemistry chemistry.chemical_compound Hydroboration Allylic rearrangement chemistry Enantioselective synthesis chemistry.chemical_element Amine gas treating Alcohol General Chemistry Copper Combinatorial chemistry Catalysis
Zdroj:	Chemical Science
ISSN:	2041-6539 2041-6520
DOI:	10.1039/d0sc03759a
Popis:	The synthesis of γ-chiral borylalkanes through copper-catalyzed enantioselective SN2′-reduction of γ,γ-disubstituted allylic substrates and subsequent hydroboration was reported. A copper–DTBM-Segphos catalyst produced a range of γ-chiral alkylboronates from easily accessible allylic acetate or benzoate with high enantioselectivities up to 99% ee. Furthermore, selective organic transformations of the resulting γ-chiral alkylboronates generated the corresponding γ-chiral alcohol, arene and amine compounds. Copper-catalyzed reductive hydroboration of γ,γ-disubstituted allylic substrates enables preparation of γ-chiral alkylboron compounds in a one-pot cascade manner.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a74e564763b2c4fe63e4292a6cd03bfa https://doi.org/10.1039/d0sc03759a Zobrazit plný text záznamu