Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

Fernando Arteaga Arteaga; Zijian Liu; Lennart Brewitz; Jianyang Chen; Bo Sun; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/acs.orglett.6b00879

Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

Fernando Arteaga Arteaga, Zijian Liu, Lennart Brewitz, Jianyang Chen, Bo Sun, Naoya Kumagai, Masakatsu Shibasaki

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

33 Citations (Scopus)

Abstract

Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.

Original language	English
Pages (from-to)	2391-2394
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.6b00879
Publication status	Published - 2016 May 20
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b00879

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title = "Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides",

abstract = "Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.",

author = "Arteaga, {Fernando Arteaga} and Zijian Liu and Lennart Brewitz and Jianyang Chen and Bo Sun and Naoya Kumagai and Masakatsu Shibasaki",

note = "Funding Information: This work was financially supported by JST, ACT-C (for M.S.), and KAKENHI (No. 25713002) from JSPS (for N.K.). N.K. thanks The Naito Foundation for financial support. Dr. Ryuichi Sawa, Ms. Yumiko Kubota, and Dr. Kiyoko Iijima at the Institute of Microbial Chemistry are gratefully acknowledged for their assistance with the NMR analysis. We thank Dr. Tomoyuki Kimura at the Institute of Microbial Chemistry for assistance with the X-ray crystallography. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = may,

day = "20",

doi = "10.1021/acs.orglett.6b00879",

language = "English",

volume = "18",

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journal = "Organic Letters",

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AU - Arteaga, Fernando Arteaga

AU - Liu, Zijian

AU - Brewitz, Lennart

AU - Chen, Jianyang

AU - Sun, Bo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

N1 - Funding Information: This work was financially supported by JST, ACT-C (for M.S.), and KAKENHI (No. 25713002) from JSPS (for N.K.). N.K. thanks The Naito Foundation for financial support. Dr. Ryuichi Sawa, Ms. Yumiko Kubota, and Dr. Kiyoko Iijima at the Institute of Microbial Chemistry are gratefully acknowledged for their assistance with the NMR analysis. We thank Dr. Tomoyuki Kimura at the Institute of Microbial Chemistry for assistance with the X-ray crystallography. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/5/20

Y1 - 2016/5/20

N2 - Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.

AB - Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.

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Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

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