Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β-Unsaturated Carbonyl Derivatives

Roxana Postolache; Juana M. Pérez; Marta Castiñeira Reis; Luo Ge; Esther G. Sinnema; Syuzanna R. Harutyunyan

doi:10.1021/acs.orglett.2c04256

Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β-Unsaturated Carbonyl Derivatives

Roxana Postolache, Juana M. Pérez, Marta Castiñeira Reis, Luo Ge, Esther G. Sinnema, Syuzanna R. Harutyunyan^*

^*Corresponding author for this work

Synthetic Organic Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

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Abstract

Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors.

Original language	English
Pages (from-to)	1611-1615
Number of pages	5
Journal	Organic letters
Volume	25
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.2c04256
Publication status	Published - 17-Mar-2023

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10.1021/acs.orglett.2c04256Licence: CC BY

Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β‑Unsaturated Carbonyl DerivativesFinal publisher's version, 1.72 MBLicence: CC BY

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@article{1691e03ba15e4b49a493bd1cdc63d1c1,

title = "Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β-Unsaturated Carbonyl Derivatives",

abstract = "Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors.",

author = "Roxana Postolache and P{\'e}rez, {Juana M.} and {Casti{\~n}eira Reis}, Marta and Luo Ge and Sinnema, {Esther G.} and Harutyunyan, {Syuzanna R.}",

note = "Funding Information: Folkert de Vries is acknowledged for the X-ray measurements. Financial support from the European Research Council (S.R.H., Grant 773264, LACOPAROM), The Netherlands Organization for Scientific Research (NWO-VICI to S.R.H.), and the China Scholarship Council (CSC, to L.G.) is acknowledged. M.C.R. thanks Xunta de Galicia (Galicia, Spain) for financial support through the ED481B-Axudas de apoio {\'a} etapa de formaci{\'o}n posdoutoral (modalidade A) fellowship. Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

year = "2023",

month = mar,

day = "17",

doi = "10.1021/acs.orglett.2c04256",

language = "English",

volume = "25",

pages = "1611--1615",

journal = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

number = "10",

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TY - JOUR

T1 - Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β-Unsaturated Carbonyl Derivatives

AU - Postolache, Roxana

AU - Pérez, Juana M.

AU - Castiñeira Reis, Marta

AU - Ge, Luo

AU - Sinnema, Esther G.

AU - Harutyunyan, Syuzanna R.

N1 - Funding Information: Folkert de Vries is acknowledged for the X-ray measurements. Financial support from the European Research Council (S.R.H., Grant 773264, LACOPAROM), The Netherlands Organization for Scientific Research (NWO-VICI to S.R.H.), and the China Scholarship Council (CSC, to L.G.) is acknowledged. M.C.R. thanks Xunta de Galicia (Galicia, Spain) for financial support through the ED481B-Axudas de apoio á etapa de formación posdoutoral (modalidade A) fellowship. Publisher Copyright: © 2023 The Authors. Published by American Chemical Society.

PY - 2023/3/17

Y1 - 2023/3/17

N2 - Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors.

AB - Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors.

UR - http://www.scopus.com/inward/record.url?scp=85149718470&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.2c04256

DO - 10.1021/acs.orglett.2c04256

M3 - Article

C2 - 36892214

AN - SCOPUS:85149718470

SN - 1523-7060

VL - 25

SP - 1611

EP - 1615

JO - Organic letters

JF - Organic letters

IS - 10

ER -

Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β-Unsaturated Carbonyl Derivatives

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CCDC 2085289: Experimental Crystal Structure Determination

CCDC 2085288: Experimental Crystal Structure Determination

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Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β-Unsaturated Carbonyl Derivatives

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CCDC 2085289: Experimental Crystal Structure Determination

CCDC 2085288: Experimental Crystal Structure Determination

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