Chiral spirosiladiphosphines: ligand development and applications in Rh-catalyzed asymmetric hydrosilylation/cyclization of 1,6-enynes with enhanced reactivity.

Fei Hou, Minjie Liu, Tong Ru, Zequn Tan, Yingtang Ning, Fen-Er Chen

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Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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6 authors.

Fei HouEngineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.

Minjie LiuEngineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.

Tong RuEngineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.

Zequn TanEngineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.

Yingtang NingEngineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.ORCID https://orcid.org/0000-0002-1035-3737

Fen-Er ChenEngineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.ORCID https://orcid.org/0000-0002-6734-3388

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No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Spirodiphosphines have been successfully applied in various asymmetric catalytic transformations. However, controlling the coordinating conformations by the direct displacement of the spiro atom remains elusive. Herein, we report the application of Si-centered spirodiphosphine (Si-SDP) ligands in the enantioselective hydrosilylation/cyclization of 1,6-enynes. The Si-SDPs showed superior reactivity to existing C2-symmetric diphosphines, allowing the generation of a range of chiral pyrrolidines with high yields and enantioselectivity (up to 96% yield and 92% ee) at room temperature with low catalyst loading. The mechanistic observations were consistent with the modified Chalk-Harrod mechanism, and the high reactivity of Si-SDPs was further leveraged for the room-temperature Rh-catalyzed hydrosilylation of alkynes.

Identifiers

PMID37152270

DOI10.1039/d2sc06349b

PMCPMC10155919

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.