Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides

Zhongdong Sun; Bo Sun; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/acs.orglett.8b01109

Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides

Zhongdong Sun, Bo Sun, Naoya Kumagai, Masakatsu Shibasaki

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

29 Citations (Scopus)

Abstract

Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides (p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.

Original language	English
Pages (from-to)	3070-3073
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.8b01109
Publication status	Published - 2018 May 18
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b01109

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title = "Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides",

abstract = "Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides (p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.",

author = "Zhongdong Sun and Bo Sun and Naoya Kumagai and Masakatsu Shibasaki",

note = "Funding Information: This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (17H03025 and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS. N.K. thanks the Naito Foundation for financial support. We thank Dr. Tomoyuki Kimura at the Institute of Microbial Chemistry for assistance with the X-ray crystallography. Funding Information: This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (17H03025 and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = may,

day = "18",

doi = "10.1021/acs.orglett.8b01109",

language = "English",

volume = "20",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides

AU - Sun, Zhongdong

AU - Sun, Bo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

N1 - Funding Information: This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (17H03025 and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS. N.K. thanks the Naito Foundation for financial support. We thank Dr. Tomoyuki Kimura at the Institute of Microbial Chemistry for assistance with the X-ray crystallography. Funding Information: This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (17H03025 and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/5/18

Y1 - 2018/5/18

N2 - Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides (p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.

AB - Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides (p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.

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Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides

Abstract

ASJC Scopus subject areas

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