Access to β2-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

Jia Hong Jian; Chih Lung Hsu; Jin Fong Syu; Ting Shen Kuo; Ming Kang Tsai; Ping Yu Wu; Hsyueh Liang Wu

doi:10.1021/acs.joc.8b00586

Access to β²-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

Jia Hong Jian, Chih Lung Hsu, Jin Fong Syu, Ting Shen Kuo, Ming Kang Tsai, Ping Yu Wu, Hsyueh Liang Wu^*

^*Corresponding author for this work

Department of Chemistry

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

22 Citations (Scopus)

Abstract

The highly enantioselective conjugate addition of a variety of arylboronic acids to β-nitroacrylates is reported to provide optically active α-aryl β-nitropropionates in up to 70% yields and >99.5% ee's, which are useful building blocks for preparing chiral β²-amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β²-amino acid 5 and transforming 3ap to β-amino ester 7 via reduction and reductive N-alkylation. The latter compound is a precursor for preparing ent-ipatasertib.

Original language	English
Pages (from-to)	12184-12191
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	83
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.8b00586
Publication status	Published - 2018 Oct 5

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.8b00586

Cite this

@article{bc712c25b12a494ca21a8ab9ab716b73,

title = "Access to β2-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts",

abstract = "The highly enantioselective conjugate addition of a variety of arylboronic acids to β-nitroacrylates is reported to provide optically active α-aryl β-nitropropionates in up to 70\% yields and >99.5\% ee's, which are useful building blocks for preparing chiral β2-amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β2-amino acid 5 and transforming 3ap to β-amino ester 7 via reduction and reductive N-alkylation. The latter compound is a precursor for preparing ent-ipatasertib.",

author = "Jian, \{Jia Hong\} and Hsu, \{Chih Lung\} and Syu, \{Jin Fong\} and Kuo, \{Ting Shen\} and Tsai, \{Ming Kang\} and Wu, \{Ping Yu\} and Wu, \{Hsyueh Liang\}",

note = "Funding Information: Financial support from the Ministry of Science and Technology of Republic of China (Grants 102-2113-M-003-006-MY2 and 104-2628-M-003-001-MY3) and National Taiwan Normal University (NTNU 2016 Subsidy Policy for International Collaboration and Research Projects) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = oct,

day = "5",

doi = "10.1021/acs.joc.8b00586",

language = "English",

volume = "83",

pages = "12184--12191",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Access to β2-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

AU - Jian, Jia Hong

AU - Hsu, Chih Lung

AU - Syu, Jin Fong

AU - Kuo, Ting Shen

AU - Tsai, Ming Kang

AU - Wu, Ping Yu

AU - Wu, Hsyueh Liang

N1 - Funding Information: Financial support from the Ministry of Science and Technology of Republic of China (Grants 102-2113-M-003-006-MY2 and 104-2628-M-003-001-MY3) and National Taiwan Normal University (NTNU 2016 Subsidy Policy for International Collaboration and Research Projects) is gratefully acknowledged. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/10/5

Y1 - 2018/10/5

N2 - The highly enantioselective conjugate addition of a variety of arylboronic acids to β-nitroacrylates is reported to provide optically active α-aryl β-nitropropionates in up to 70% yields and >99.5% ee's, which are useful building blocks for preparing chiral β2-amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β2-amino acid 5 and transforming 3ap to β-amino ester 7 via reduction and reductive N-alkylation. The latter compound is a precursor for preparing ent-ipatasertib.

AB - The highly enantioselective conjugate addition of a variety of arylboronic acids to β-nitroacrylates is reported to provide optically active α-aryl β-nitropropionates in up to 70% yields and >99.5% ee's, which are useful building blocks for preparing chiral β2-amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β2-amino acid 5 and transforming 3ap to β-amino ester 7 via reduction and reductive N-alkylation. The latter compound is a precursor for preparing ent-ipatasertib.

UR - https://www.scopus.com/pages/publications/85053631008

UR - https://www.scopus.com/inward/citedby.url?scp=85053631008&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b00586

DO - 10.1021/acs.joc.8b00586

M3 - Article

C2 - 30153730

AN - SCOPUS:85053631008

SN - 0022-3263

VL - 83

SP - 12184

EP - 12191

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Access to β²-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

Abstract

ASJC Scopus subject areas

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CCDC 1820490: Experimental Crystal Structure Determination

CCDC 1820488: Experimental Crystal Structure Determination

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Access to β2-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1820490: Experimental Crystal Structure Determination

CCDC 1820488: Experimental Crystal Structure Determination

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Access to β²-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts