Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade

Jia Hong Jian; Hao Wei Zeng; Ting Shen Kuo; Ping Yu Wu; Hsyueh Liang Wu

doi:10.1021/acs.orglett.9b03666

Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade

Jia Hong Jian, Hao Wei Zeng, Ting Shen Kuo, Ping Yu Wu, Hsyueh Liang Wu^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

13 引文斯高帕斯（Scopus）

摘要

The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.

原文	英語
頁（從 - 到）	9468-9472
頁數	5
期刊	Organic Letters
卷	21
發行號	23
DOIs	https://doi.org/10.1021/acs.orglett.9b03666
出版狀態	已發佈 - 2019 12月 6

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

存取文件

10.1021/acs.orglett.9b03666

其它文件與鏈接

CCDC 1959338: Experimental Crystal Structure Determination
Jian, J. (Contributor), Zeng, H. (Contributor), Kuo, T. (Contributor), Wu, P. (Contributor) & Wu, H. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc23rvg6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23rvg6&sid=DataCite
資料集: Dataset

引用此

@article{61fe8ab03c6b4cbcad71ac9dd20e88cf,

title = "Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade",

abstract = "The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.",

author = "Jian, {Jia Hong} and Zeng, {Hao Wei} and Kuo, {Ting Shen} and Wu, {Ping Yu} and Wu, {Hsyueh Liang}",

note = "Funding Information: Financial support from the Ministry of Science and Technology of the Republic of China (104-2628-M-003-001-MY3 and 107-2113-M-003-014-MY3) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = dec,

day = "6",

doi = "10.1021/acs.orglett.9b03666",

language = "English",

volume = "21",

pages = "9468--9472",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade

AU - Jian, Jia Hong

AU - Zeng, Hao Wei

AU - Kuo, Ting Shen

AU - Wu, Ping Yu

AU - Wu, Hsyueh Liang

N1 - Funding Information: Financial support from the Ministry of Science and Technology of the Republic of China (104-2628-M-003-001-MY3 and 107-2113-M-003-014-MY3) is gratefully acknowledged. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/12/6

Y1 - 2019/12/6

N2 - The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.

AB - The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.

UR - http://www.scopus.com/inward/record.url?scp=85075430397&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85075430397&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b03666

DO - 10.1021/acs.orglett.9b03666

M3 - Article

C2 - 31742418

AN - SCOPUS:85075430397

VL - 21

SP - 9468

EP - 9472

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 23

ER -

Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1959338: Experimental Crystal Structure Determination

引用此