Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction

Kazuhiro Tsuna; Naoyoshi Noguchi; Masahisa Nakada

doi:10.1016/j.tetlet.2011.10.148

Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction

Kazuhiro Tsuna, Naoyoshi Noguchi, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

7 Citations (Scopus)

Abstract

Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction is described. The sequence of hydroboration of ω-alkenyl thiol ester with 9-BBN and the Liebeskind-Srogl reaction results in the formation of medium-sized carbocyclic ketones with good yield.

Original language	English
Pages (from-to)	7202-7205
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.148
Publication status	Published - 2011 Dec 28

Keywords

Intramolecular coupling reaction
Liebeskind-Srogl coupling reaction
Medium-sized carbocyclic ketone
Palladium-mediated reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.10.148

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title = "Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction",

abstract = "Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction is described. The sequence of hydroboration of ω-alkenyl thiol ester with 9-BBN and the Liebeskind-Srogl reaction results in the formation of medium-sized carbocyclic ketones with good yield.",

keywords = "Intramolecular coupling reaction, Liebeskind-Srogl coupling reaction, Medium-sized carbocyclic ketone, Palladium-mediated reaction",

author = "Kazuhiro Tsuna and Naoyoshi Noguchi and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research on Innovative Areas (No. 21106009), Young Scientists (No. 19890231), and the Global COE program “Center for Practical Chemical Wisdom” by MEXT. ",

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doi = "10.1016/j.tetlet.2011.10.148",

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T1 - Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction

AU - Tsuna, Kazuhiro

AU - Noguchi, Naoyoshi

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research on Innovative Areas (No. 21106009), Young Scientists (No. 19890231), and the Global COE program “Center for Practical Chemical Wisdom” by MEXT.

PY - 2011/12/28

Y1 - 2011/12/28

N2 - Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction is described. The sequence of hydroboration of ω-alkenyl thiol ester with 9-BBN and the Liebeskind-Srogl reaction results in the formation of medium-sized carbocyclic ketones with good yield.

AB - Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction is described. The sequence of hydroboration of ω-alkenyl thiol ester with 9-BBN and the Liebeskind-Srogl reaction results in the formation of medium-sized carbocyclic ketones with good yield.

KW - Intramolecular coupling reaction

KW - Liebeskind-Srogl coupling reaction

KW - Medium-sized carbocyclic ketone

KW - Palladium-mediated reaction

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DO - 10.1016/j.tetlet.2011.10.148

M3 - Article

AN - SCOPUS:82255193951

SN - 0040-4039

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EP - 7205

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind-Srogl coupling reaction

Abstract

Keywords

ASJC Scopus subject areas

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