Synlett 2022; 33(20): 2019-2025
DOI: 10.1055/a-1955-2016
letter

Enantioselective Synthesis of α-Hydroxyamino Ketones by a Chiral Phosphine–Silver Complex Catalyzed N-Nitroso Aldol Reaction

Akira Yanagisawa
,
Shiho Kasahara
,
Akihiro Takeishi
,
Tomoki Marui
This work was supported by the Ministry of Education, Culture, Sports, Science and Technology (MEXT) and the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant Numbers 16K05766 and 19K05450). We acknowledge the generous gift of (R)-DTBM-SEGPHOS from Takasago International Corporation. We also gratefully acknowledge the financial support from Nippoh Chemicals Co., Ltd.


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Abstract

A catalytic asymmetric N-nitroso aldol reaction of alkenyl trifluoroacetates with nitrosoarenes was achieved using a DTBM-SEGPHOS·AgOTf complex as the chiral precatalyst and KHMDS as the base precatalyst in the presence of methanol. Optically active α-hydroxyamino ketones with up to 89% ee were regioselectively obtained in moderate to high yields not only from acyclic alkenyl esters but also from cyclic ones through the in situ generated chiral silver enolates.

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Publication History

Received: 20 September 2022

Accepted after revision: 05 October 2022

Accepted Manuscript online:
05 October 2022

Article published online:
03 November 2022

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