Stereodivergent Dual Catalytic α-Allylation of Protected α-Amino- and α-Hydroxyacetaldehydes

Autor:	Erick M. Carreira, Hannes F. Zipfel, Simon Krautwald, Tobias Sandmeier
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Allylic rearrangement chemistry Stereochemistry High selectivity chemistry.chemical_element General Chemistry Iridium Aldehyde Combinatorial chemistry Catalysis
Zdroj:	Angewandte Chemie (International ed. in English). 54(48)
ISSN:	1521-3773
Popis:	Fully stereodivergent dual-catalytic α-allylation of protected α-amino- and α-hydroxyacetaldehydes is achieved through iridium- and amine-catalyzed substitution of racemic allylic alcohols with chiral enamines generated in situ. The operationally simple method furnishes useful aldehyde building blocks in good yields, more than 99% ee, and with d.r. values greater than 20:1 in some cases. Additionally, the γ,δ-unsaturated products can be further functionalized in a stereodivergent fashion with high selectivity and with preservation of stereochemical integrity at the Cα position.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d3eb04c1bd1738704d2f76d1047497ee https://pubmed.ncbi.nlm.nih.gov/26427612 Zobrazit plný text záznamu Plný text