Construction of a new type of chiral bidentate NHC ligands: copper-catalyzed asymmetric conjugate alkylation

Tatsuya Uchida; Tsutomu Katsuki

doi:10.1016/j.tetlet.2009.06.026

Construction of a new type of chiral bidentate NHC ligands: copper-catalyzed asymmetric conjugate alkylation

Tatsuya Uchida, Tsutomu Katsuki

Division for Experimental Natural Science

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

44 Citations (Scopus)

Abstract

We synthesized in three steps simple chiral bidentate NHC compounds that carry an achiral coordinating group as N-substituent and revealed that they serve as efficient chiral auxiliaries for the copper-catalyzed asymmetric conjugate addition of dialkylzinc to acyclic enones (up to 97% ee).

Original language	English
Pages (from-to)	4741-4743
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2009.06.026
Publication status	Published - Aug 18 2009

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.06.026

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title = "Construction of a new type of chiral bidentate NHC ligands: copper-catalyzed asymmetric conjugate alkylation",

abstract = "We synthesized in three steps simple chiral bidentate NHC compounds that carry an achiral coordinating group as N-substituent and revealed that they serve as efficient chiral auxiliaries for the copper-catalyzed asymmetric conjugate addition of dialkylzinc to acyclic enones (up to 97% ee).",

author = "Tatsuya Uchida and Tsutomu Katsuki",

note = "Funding Information: The authors acknowledge the financial support from a Grant-in-Aid for Scientific Research on Priority Areas 18037056 {\textquoteleft}Advanced Molecular Transformations of Carbon Resources{\textquoteright} and Specially Promoted Research 18002011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

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doi = "10.1016/j.tetlet.2009.06.026",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Construction of a new type of chiral bidentate NHC ligands

T2 - copper-catalyzed asymmetric conjugate alkylation

AU - Uchida, Tatsuya

AU - Katsuki, Tsutomu

N1 - Funding Information: The authors acknowledge the financial support from a Grant-in-Aid for Scientific Research on Priority Areas 18037056 ‘Advanced Molecular Transformations of Carbon Resources’ and Specially Promoted Research 18002011 from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2009/8/18

Y1 - 2009/8/18

N2 - We synthesized in three steps simple chiral bidentate NHC compounds that carry an achiral coordinating group as N-substituent and revealed that they serve as efficient chiral auxiliaries for the copper-catalyzed asymmetric conjugate addition of dialkylzinc to acyclic enones (up to 97% ee).

AB - We synthesized in three steps simple chiral bidentate NHC compounds that carry an achiral coordinating group as N-substituent and revealed that they serve as efficient chiral auxiliaries for the copper-catalyzed asymmetric conjugate addition of dialkylzinc to acyclic enones (up to 97% ee).

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DO - 10.1016/j.tetlet.2009.06.026

M3 - Article

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SN - 0040-4039

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EP - 4743

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Construction of a new type of chiral bidentate NHC ligands: copper-catalyzed asymmetric conjugate alkylation

Abstract

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