Asymmetric Multicomponent Reactions for Efficient Construction of Homopropargyl Amine Carboxylic Esters

Sifan Yu; Ruyu Hua; Xiang Fu; Gengxin  Liu; Dan  Zhang; Shikun Jia; Huang Qiu; Wenhao Hu

doi:10.1021/acs.orglett.9b02139

Asymmetric Multicomponent Reactions for Efficient Construction of Homopropargyl Amine Carboxylic Esters

Sifan Yu, Ruyu Hua, Xiang Fu, Gengxin Liu, Dan Zhang, Shikun Jia, Huang Qiu^*, Wenhao Hu^*

^*Corresponding author for this work

Chinese Medicine - Teaching and Research Division

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

40 Citations (Scopus)

Abstract

Developing an efficient and highly enantioselective protocol to access homopropargyl amines is of high interest to the synthetic community and also remains a formidable challenge for organic chemists. Here, we present integrated Rh₂(OAc)₄- and BINOL-derived chiral phosphoric acid cooperatively catalyzed three-component reactions of alkynyldiazoacetates, imines with various nucleophiles including alcohols, indoles, and N,N-disubstituted anilines, affording the corresponding homopropargyl amines containing two vicinal chiral centers in satisfactory yields with high to excellent diastereo- and enantioselectivities.

Original language	English
Pages (from-to)	5737-5741
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.9b02139
Publication status	Published - 19 Jul 2019

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title = "Asymmetric Multicomponent Reactions for Efficient Construction of Homopropargyl Amine Carboxylic Esters",

abstract = "Developing an efficient and highly enantioselective protocol to access homopropargyl amines is of high interest to the synthetic community and also remains a formidable challenge for organic chemists. Here, we present integrated Rh2(OAc)4- and BINOL-derived chiral phosphoric acid cooperatively catalyzed three-component reactions of alkynyldiazoacetates, imines with various nucleophiles including alcohols, indoles, and N,N-disubstituted anilines, affording the corresponding homopropargyl amines containing two vicinal chiral centers in satisfactory yields with high to excellent diastereo- and enantioselectivities.",

author = "Sifan Yu and Ruyu Hua and Xiang Fu and Gengxin Liu and Dan Zhang and Shikun Jia and Huang Qiu and Wenhao Hu",

note = "Funding Information: We acknowledge financial support from the Guangdong Innovative and Entrepreneurial Research Team Program (No. 2016ZT06Y337), National Natural Science Foundation of China (21801255), National Science & Technology Major Project (2018ZX09711002-006), and Natural Science Foundation of Guangdong Province (2018A030310141). Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b02139",

language = "English",

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journal = "Organic Letters",

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TY - JOUR

T1 - Asymmetric Multicomponent Reactions for Efficient Construction of Homopropargyl Amine Carboxylic Esters

AU - Yu, Sifan

AU - Hua, Ruyu

AU - Fu, Xiang

AU - Liu, Gengxin

AU - Zhang, Dan

AU - Jia, Shikun

AU - Qiu, Huang

AU - Hu, Wenhao

N1 - Funding Information: We acknowledge financial support from the Guangdong Innovative and Entrepreneurial Research Team Program (No. 2016ZT06Y337), National Natural Science Foundation of China (21801255), National Science & Technology Major Project (2018ZX09711002-006), and Natural Science Foundation of Guangdong Province (2018A030310141). Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/7/19

Y1 - 2019/7/19

N2 - Developing an efficient and highly enantioselective protocol to access homopropargyl amines is of high interest to the synthetic community and also remains a formidable challenge for organic chemists. Here, we present integrated Rh2(OAc)4- and BINOL-derived chiral phosphoric acid cooperatively catalyzed three-component reactions of alkynyldiazoacetates, imines with various nucleophiles including alcohols, indoles, and N,N-disubstituted anilines, affording the corresponding homopropargyl amines containing two vicinal chiral centers in satisfactory yields with high to excellent diastereo- and enantioselectivities.

AB - Developing an efficient and highly enantioselective protocol to access homopropargyl amines is of high interest to the synthetic community and also remains a formidable challenge for organic chemists. Here, we present integrated Rh2(OAc)4- and BINOL-derived chiral phosphoric acid cooperatively catalyzed three-component reactions of alkynyldiazoacetates, imines with various nucleophiles including alcohols, indoles, and N,N-disubstituted anilines, affording the corresponding homopropargyl amines containing two vicinal chiral centers in satisfactory yields with high to excellent diastereo- and enantioselectivities.

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U2 - 10.1021/acs.orglett.9b02139

DO - 10.1021/acs.orglett.9b02139

M3 - Journal article

SN - 1523-7060

VL - 21

SP - 5737

EP - 5741

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Asymmetric Multicomponent Reactions for Efficient Construction of Homopropargyl Amine Carboxylic Esters

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