Enantioselective Catalytic Synthesis of α‐Stereogenic Chromen‐4‐one Amino Derivatives

Enantioselective Catalytic Synthesis of α‐Stereogenic Chromen‐4‐one Amino Derivatives Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2023, Volume: 365, Number: 18, Pages: 3162-3166 Pages count : 5 DOI: 10.1002/adsc.202300659

Authors

Kovalevsky Ruslan ^1,2 , Vasechkin Konstantin V. ^2,3 , Kucherenko Alexander ² , Zlotin Sergei ²

Affiliations

1	M. V. Lomonosov Moscow State University Department of Chemistry Leninskie gory 1–3 119234 Moscow Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky Prospect 119991 Moscow Russian Federation
3	Institute of Pharmacy Sechenov First Moscow State Medical University Trubetskaya Str. 8/2 119991 Moscow Russian Federation

Direct enantioselective synthesis of 2-substituted chromen-4-ones, bearing the amino group at α-stereogenic center with respect to the heterocycle is developed. It is based on Mannich-type asymmetric addition of 3-hydroxychromen-4-one and its analogues to N-protected imines in the presence of available alkaloid dihydrocuprein. α-Stereogenic chromenone amino derivatives were formed in this reactions in 81–95% yield with up to 98% ee. The chiral adducts were transformed to diverse enantiomerically enriched chromen-4-one functional derivatives.

Kovalevsky R. , Vasechkin K.V. , Kucherenko A. , Zlotin S.
Enantioselective Catalytic Synthesis of α‐Stereogenic Chromen‐4‐one Amino Derivatives
Advanced Synthesis & Catalysis. 2023. V.365. N18. P.3162-3166. DOI: 10.1002/adsc.202300659 WOS Scopus OpenAlex

Web of science:	WOS:001045142800001
Scopus:	2-s2.0-85167661202
OpenAlex:	W4385481624

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OpenAlex	4
Scopus	4
Web of science	4