Copper-dipyridylphosphine-catalyzed hydrosilylation: Enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols

Shan Bin Qi; Min Li; Shijun Li; Ji Ning Zhou; Jun Wen Wu; Feng Yu; Xi Chang Zhang; Albert S.C. Chan; Jing Wu

doi:10.1039/c2ob27040d

Copper-dipyridylphosphine-catalyzed hydrosilylation: Enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols

Shan Bin Qi
, Min Li
, Shijun Li
, Ji Ning Zhou
, Jun Wen Wu
, Feng Yu
, Xi Chang Zhang
, Albert S.C. Chan
, Jing Wu^*

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the steric size of cycloalkyl groups has a significant influence on the reaction outcomes. The first stereoselective formation of a selection of cyclohexyl heteroaryl alcohols of up to 97% enantiopurity was realized as well. Dramatic temperature effects on both the enantiopurity and the absolute configuration of the alcohol products were observed in the reduction of some cyclohexyl pyridyl ketones.

Original language	English
Pages (from-to)	929-937
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	6
Early online date	29 Nov 2012
DOIs	https://doi.org/10.1039/c2ob27040d
Publication status	Published - 14 Feb 2013

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10.1039/c2ob27040d

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@article{e1d3a5060d384962b8b87d87ae4562e9,

title = "Copper-dipyridylphosphine-catalyzed hydrosilylation: Enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols",

abstract = "The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99\% enantiomeric excess). The results demonstrated that the steric size of cycloalkyl groups has a significant influence on the reaction outcomes. The first stereoselective formation of a selection of cyclohexyl heteroaryl alcohols of up to 97\% enantiopurity was realized as well. Dramatic temperature effects on both the enantiopurity and the absolute configuration of the alcohol products were observed in the reduction of some cyclohexyl pyridyl ketones.",

author = "Qi, \{Shan Bin\} and Min Li and Shijun Li and Zhou, \{Ji Ning\} and Wu, \{Jun Wen\} and Feng Yu and Zhang, \{Xi Chang\} and Chan, \{Albert S.C.\} and Jing Wu",

note = "We thank the National Natural Science Foundation of China (21172049, 91127010, 21032003, 21072039), the Public Welfare Technology and Application Program of Zhejiang Province (2010C31042) and the Special Funds for Key Innovation Team of Zhejiang Province (2010R50017) for generous financial support of this research. Publisher copyright: {\textcopyright} The Royal Society of Chemistry 2013",

year = "2013",

month = feb,

day = "14",

doi = "10.1039/c2ob27040d",

language = "English",

volume = "11",

pages = "929--937",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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}

TY - JOUR

T1 - Copper-dipyridylphosphine-catalyzed hydrosilylation

T2 - Enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols

AU - Qi, Shan Bin

AU - Li, Min

AU - Li, Shijun

AU - Zhou, Ji Ning

AU - Wu, Jun Wen

AU - Yu, Feng

AU - Zhang, Xi Chang

AU - Chan, Albert S.C.

AU - Wu, Jing

N1 - We thank the National Natural Science Foundation of China (21172049, 91127010, 21032003, 21072039), the Public Welfare Technology and Application Program of Zhejiang Province (2010C31042) and the Special Funds for Key Innovation Team of Zhejiang Province (2010R50017) for generous financial support of this research. Publisher copyright: © The Royal Society of Chemistry 2013

PY - 2013/2/14

Y1 - 2013/2/14

N2 - The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the steric size of cycloalkyl groups has a significant influence on the reaction outcomes. The first stereoselective formation of a selection of cyclohexyl heteroaryl alcohols of up to 97% enantiopurity was realized as well. Dramatic temperature effects on both the enantiopurity and the absolute configuration of the alcohol products were observed in the reduction of some cyclohexyl pyridyl ketones.

AB - The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the steric size of cycloalkyl groups has a significant influence on the reaction outcomes. The first stereoselective formation of a selection of cyclohexyl heteroaryl alcohols of up to 97% enantiopurity was realized as well. Dramatic temperature effects on both the enantiopurity and the absolute configuration of the alcohol products were observed in the reduction of some cyclohexyl pyridyl ketones.

UR - https://www.scopus.com/pages/publications/84872695512

U2 - 10.1039/c2ob27040d

DO - 10.1039/c2ob27040d

M3 - Journal article

C2 - 23247695

AN - SCOPUS:84872695512

SN - 1477-0520

VL - 11

SP - 929

EP - 937

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

Copper-dipyridylphosphine-catalyzed hydrosilylation: Enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols

Abstract

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