Catalytic, enantioselective, conjugate alkyne addition

Thomas F. Knöpfel; Pablo Zarotti; Takashi Ichikawa; Erick M. Carreira

doi:10.1021/ja052411r

Catalytic, enantioselective, conjugate alkyne addition

Thomas F. Knöpfel, Pablo Zarotti, Takashi Ichikawa, Erick M. Carreira^*

^*Corresponding author for this work

Department of Physics

Research output: Contribution to journal › Journal article › peer-review

188 Citations (Scopus)

Abstract

We document a copper-catalyzed, enantioselective, conjugate addition involving the direct use of a terminal acetylene, which undergoes in situ metalation. The addition reactions of phenylacetylene to Meldrum's acid derived acceptors take place in aqueous media, without recourse to inert atmosphere. The success of the enantioselective process was enabled by the use of a new class of conveniently accessed P,N-ligands, which we have termed PINAP. These modular ligands are responsive to numerous electronic and steric modifications that permit optimization of the reaction.

Original language	English
Pages (from-to)	9682-9683
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	27
DOIs	https://doi.org/10.1021/ja052411r
Publication status	Published - 13 Jul 2005

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title = "Catalytic, enantioselective, conjugate alkyne addition",

abstract = "We document a copper-catalyzed, enantioselective, conjugate addition involving the direct use of a terminal acetylene, which undergoes in situ metalation. The addition reactions of phenylacetylene to Meldrum's acid derived acceptors take place in aqueous media, without recourse to inert atmosphere. The success of the enantioselective process was enabled by the use of a new class of conveniently accessed P,N-ligands, which we have termed PINAP. These modular ligands are responsive to numerous electronic and steric modifications that permit optimization of the reaction.",

author = "Kn{\"o}pfel, {Thomas F.} and Pablo Zarotti and Takashi Ichikawa and Carreira, {Erick M.}",

note = "We are grateful for the support of Sumitomo Chemical Co., Ltd., Fine Chemicals Research Laboratory. We thank Dr. B. Schweizer for the determination of the X-ray structures. Publisher Copyright: {\textcopyright} 2005 American Chemical Society",

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doi = "10.1021/ja052411r",

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T1 - Catalytic, enantioselective, conjugate alkyne addition

AU - Knöpfel, Thomas F.

AU - Zarotti, Pablo

AU - Ichikawa, Takashi

AU - Carreira, Erick M.

N1 - We are grateful for the support of Sumitomo Chemical Co., Ltd., Fine Chemicals Research Laboratory. We thank Dr. B. Schweizer for the determination of the X-ray structures. Publisher Copyright: © 2005 American Chemical Society

PY - 2005/7/13

Y1 - 2005/7/13

N2 - We document a copper-catalyzed, enantioselective, conjugate addition involving the direct use of a terminal acetylene, which undergoes in situ metalation. The addition reactions of phenylacetylene to Meldrum's acid derived acceptors take place in aqueous media, without recourse to inert atmosphere. The success of the enantioselective process was enabled by the use of a new class of conveniently accessed P,N-ligands, which we have termed PINAP. These modular ligands are responsive to numerous electronic and steric modifications that permit optimization of the reaction.

AB - We document a copper-catalyzed, enantioselective, conjugate addition involving the direct use of a terminal acetylene, which undergoes in situ metalation. The addition reactions of phenylacetylene to Meldrum's acid derived acceptors take place in aqueous media, without recourse to inert atmosphere. The success of the enantioselective process was enabled by the use of a new class of conveniently accessed P,N-ligands, which we have termed PINAP. These modular ligands are responsive to numerous electronic and steric modifications that permit optimization of the reaction.

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DO - 10.1021/ja052411r

M3 - Journal article

AN - SCOPUS:22144481646

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VL - 127

SP - 9682

EP - 9683

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 27

ER -

Catalytic, enantioselective, conjugate alkyne addition

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