Chiral Primary Amine Catalyzed Enantioselective Tandem Reactions Based on Heyns Rearrangement: Synthesis of α-Tertiary Amino Ketones

Autor:	Xiao-kang Nie, Yue Chen, Shi-qi Zhang, Xin Cui, Zhuo Tang, Guang-xun Li
Rok vydání:	2022
Předmět:	Organic Chemistry Stereoisomerism Amines Ketones Physical and Theoretical Chemistry Biochemistry Catalysis
Zdroj:	Organic Letters. 24:2069-2074
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.2c00724
Popis:	Herein, we disclose a new catalytic asymmetric tandem reaction based on the Heyns rearrangement for the synthesis of chiral α-amino ketones with readily available substrates. The rearrangement is different from the Heyns rearrangement in that the α-amino ketones were obtained without the shift of the carbonyl group. The key to success is using chiral primary amine as a catalyst by mimicking glucosamine-6-phosphate synthase in catalyzing the efficient Heyns rearrangement in organisms.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a69df2d7322f8f0b46f7655b990ecb78 https://doi.org/10.1021/acs.orglett.2c00724 Zobrazit plný text záznamu