Issue 6, 2023, Issue in Progress

Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines

Abstract

Catalytic functionality of new optically active thiourea fused γ-amino alcohols was examined in the asymmetric Mannich reaction of β-keto active methylene compounds with imines to afford chiral Mannich products, β-amino keto compounds, with continuous chiral centers, that are versatile synthetic intermediates for deriving various biologically active compounds. In particular, the thiourea fused γ-amino alcohols showed satisfactory catalytic activity in this reaction and afforded chiral Mannich products in excellent chemical yield (up to 88%) and stereoselectivities (up to syn : anti/93 : 7 dr, up to 99% ee).

Graphical abstract: Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines

Supplementary files

Article information

Article type
Paper
Submitted
30 Dec 2022
Accepted
18 Jan 2023
First published
26 Jan 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 3715-3722

Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines

M. Nomura, Z. Begum, C. Seki, Y. Okuyama, E. Kwon, K. Uwai, M. Tokiwa, S. Tokiwa, M. Takeshita and H. Nakano, RSC Adv., 2023, 13, 3715 DOI: 10.1039/D2RA08317E

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