Rh-Catalyzed Enantioselective and Regioselective Addition of Phosphinoylacetic Acid to Allenes

Yanxin Jiang; Zhiwu Lu; Xinzhu Yuan; Zhiping Yang; Jun (Joelle) Wang

doi:10.1002/cctc.70870

Rh-Catalyzed Enantioselective and Regioselective Addition of Phosphinoylacetic Acid to Allenes

Yanxin Jiang
, Zhiwu Lu
, Xinzhu Yuan
, Zhiping Yang^*
, Jun (Joelle) Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

Abstract

A Rh-catalyzed enantioselective addition of phosphinoylacetic acid to allenes is developed, delivering branched allylic esters as the predominant regioisomers. A broad range of allenes and phosphinoylacetic acid are tolerated, providing the products in good yields with high regio- and enantioselectivities. The method enables late-stage functionalization of cholesterol derivative and provides enantiopure five-membered lactones via a sequential Horner-Wadsworth-Emmons olefination/ring-closing metathesis sequence.

Original language	English
Article number	e70870
Number of pages	7
Journal	ChemCatChem
Volume	18
Issue number	12
Early online date	24 Jun 2026
DOIs	https://doi.org/10.1002/cctc.70870
Publication status	Published - 26 Jun 2026

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

User-Defined Keywords

Allylic esters
Enantioselectivity
Phosphorus
Regioselectivity
Rh catalysis

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10.1002/cctc.70870

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@article{1550d82e3ad3490b95c4cf10b00b81f7,

title = "Rh-Catalyzed Enantioselective and Regioselective Addition of Phosphinoylacetic Acid to Allenes",

abstract = "A Rh-catalyzed enantioselective addition of phosphinoylacetic acid to allenes is developed, delivering branched allylic esters as the predominant regioisomers. A broad range of allenes and phosphinoylacetic acid are tolerated, providing the products in good yields with high regio- and enantioselectivities. The method enables late-stage functionalization of cholesterol derivative and provides enantiopure five-membered lactones via a sequential Horner-Wadsworth-Emmons olefination/ring-closing metathesis sequence.",

keywords = "Allylic esters, Enantioselectivity, Phosphorus, Regioselectivity, Rh catalysis",

author = "Yanxin Jiang and Zhiwu Lu and Xinzhu Yuan and Zhiping Yang and Wang, \{Jun (Joelle)\}",

note = "We gratefully thank the University Grants Committee (Hong Kong) (SRFS2526-2S02), and HKBU RC-SFCRG/23-24 for financial support. Z. Yang acknowledges the support of K. C. Wong Education Foundation. We thank Dr. Xiaoyong Chang from SUSTech for x-ray crystallographic analysis. We also acknowledge facility support from the Advanced Life Sciences and Mass Spectrometry Laboratory (LSMS) of HKBU. Publisher Copyright: {\textcopyright} 2026 The Author(s). ChemCatChem published by Wiley-VCH GmbH.",

year = "2026",

month = jun,

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doi = "10.1002/cctc.70870",

language = "English",

volume = "18",

journal = "ChemCatChem",

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TY - JOUR

T1 - Rh-Catalyzed Enantioselective and Regioselective Addition of Phosphinoylacetic Acid to Allenes

AU - Jiang, Yanxin

AU - Lu, Zhiwu

AU - Yuan, Xinzhu

AU - Yang, Zhiping

AU - Wang, Jun (Joelle)

N1 - We gratefully thank the University Grants Committee (Hong Kong) (SRFS2526-2S02), and HKBU RC-SFCRG/23-24 for financial support. Z. Yang acknowledges the support of K. C. Wong Education Foundation. We thank Dr. Xiaoyong Chang from SUSTech for x-ray crystallographic analysis. We also acknowledge facility support from the Advanced Life Sciences and Mass Spectrometry Laboratory (LSMS) of HKBU. Publisher Copyright: © 2026 The Author(s). ChemCatChem published by Wiley-VCH GmbH.

PY - 2026/6/26

Y1 - 2026/6/26

N2 - A Rh-catalyzed enantioselective addition of phosphinoylacetic acid to allenes is developed, delivering branched allylic esters as the predominant regioisomers. A broad range of allenes and phosphinoylacetic acid are tolerated, providing the products in good yields with high regio- and enantioselectivities. The method enables late-stage functionalization of cholesterol derivative and provides enantiopure five-membered lactones via a sequential Horner-Wadsworth-Emmons olefination/ring-closing metathesis sequence.

AB - A Rh-catalyzed enantioselective addition of phosphinoylacetic acid to allenes is developed, delivering branched allylic esters as the predominant regioisomers. A broad range of allenes and phosphinoylacetic acid are tolerated, providing the products in good yields with high regio- and enantioselectivities. The method enables late-stage functionalization of cholesterol derivative and provides enantiopure five-membered lactones via a sequential Horner-Wadsworth-Emmons olefination/ring-closing metathesis sequence.

KW - Allylic esters

KW - Enantioselectivity

KW - Phosphorus

KW - Regioselectivity

KW - Rh catalysis

UR - https://www.scopus.com/pages/publications/105042786117

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U2 - 10.1002/cctc.70870

DO - 10.1002/cctc.70870

M3 - Journal article

SN - 1867-3880

VL - 18

JO - ChemCatChem

JF - ChemCatChem

IS - 12

M1 - e70870

ER -

Rh-Catalyzed Enantioselective and Regioselective Addition of Phosphinoylacetic Acid to Allenes

Abstract

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