Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl aryl ketones

Eiji Yamamoto; Ryoto Kojima; Koji Kubota; Hajime Ito

doi:10.1055/s-0035-1560721

Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl aryl ketones

Eiji Yamamoto, Ryoto Kojima, Koji Kubota, Hajime Ito

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

12 Citations (Scopus)

Abstract

Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl ketones with bis(pinacolato)diboron is reported. The reaction of alkenyl aryl ketones under a CuCl/Xantphos catalyst system provides four- or five-membered-ring syn-2-(borylmethyl)cycloalkanol derivatives in good yields with high syn selectivities. The utility of this method is demonstrated by further transformations of the cyclic products.

Original language	English
Article number	st-2015-u0477-l
Pages (from-to)	272-276
Number of pages	5
Journal	Synlett
Volume	27
Issue number	2
DOIs	https://doi.org/10.1055/s-0035-1560721
Publication status	Published - Jan 23 2016
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-0035-1560721

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title = "Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl aryl ketones",

abstract = "Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl ketones with bis(pinacolato)diboron is reported. The reaction of alkenyl aryl ketones under a CuCl/Xantphos catalyst system provides four- or five-membered-ring syn-2-(borylmethyl)cycloalkanol derivatives in good yields with high syn selectivities. The utility of this method is demonstrated by further transformations of the cyclic products.",

author = "Eiji Yamamoto and Ryoto Kojima and Koji Kubota and Hajime Ito",

note = "Funding Information: This work was financially supported by the NEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University. This work was also supported by JSPS KAKENHI Grant Numbers 15H03804 and 15K13633. This work was supported by JSPS KAKENHI Grant number 26·2447. E.Y. was supported by Grant-in-Aid for JSPS Fellows. Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart · New York.",

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doi = "10.1055/s-0035-1560721",

language = "English",

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T1 - Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl aryl ketones

AU - Yamamoto, Eiji

AU - Kojima, Ryoto

AU - Kubota, Koji

AU - Ito, Hajime

N1 - Funding Information: This work was financially supported by the NEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University. This work was also supported by JSPS KAKENHI Grant Numbers 15H03804 and 15K13633. This work was supported by JSPS KAKENHI Grant number 26·2447. E.Y. was supported by Grant-in-Aid for JSPS Fellows. Publisher Copyright: © Georg Thieme Verlag Stuttgart · New York.

PY - 2016/1/23

Y1 - 2016/1/23

N2 - Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl ketones with bis(pinacolato)diboron is reported. The reaction of alkenyl aryl ketones under a CuCl/Xantphos catalyst system provides four- or five-membered-ring syn-2-(borylmethyl)cycloalkanol derivatives in good yields with high syn selectivities. The utility of this method is demonstrated by further transformations of the cyclic products.

AB - Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl ketones with bis(pinacolato)diboron is reported. The reaction of alkenyl aryl ketones under a CuCl/Xantphos catalyst system provides four- or five-membered-ring syn-2-(borylmethyl)cycloalkanol derivatives in good yields with high syn selectivities. The utility of this method is demonstrated by further transformations of the cyclic products.

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M1 - st-2015-u0477-l

ER -

Copper(I)-catalyzed diastereoselective borylative exo-cyclization of alkenyl aryl ketones

Abstract

All Science Journal Classification (ASJC) codes

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