Chiral sodium phosphate catalyzed enantioselective 1,4-addition of TMSCN to aromatic enones

Jingya Yang; Shaoxiang Wu; Fu Xue Chen

doi:10.1055/s-0030-1258817

Chiral sodium phosphate catalyzed enantioselective 1,4-addition of TMSCN to aromatic enones

Jingya Yang, Shaoxiang Wu, Fu Xue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

37 Citations (Scopus)

Abstract

A facile enantioselective 1,4-addition of TMSCN to aromatic enones has been developed using chiral sodium phosphate. Thus, in the presence of 20 mol% of sodium salt generated in situ from (R)-3,3′-di(1-adamantyl)-1,1′- binaphthyl-2,2′-diylphosphoric acid and NaOH, β-cyano ketones were obtained in high yield (86-96%) and up to 72% ee within three hours at 80 °C in toluene.

Original language	English
Pages (from-to)	2725-2728
Number of pages	4
Journal	Synlett
Issue number	18
DOIs	https://doi.org/10.1055/s-0030-1258817
Publication status	Published - 2010

Keywords

1,4-addition
asymmetric catalysis
enones
nitriles
phosphates

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title = "Chiral sodium phosphate catalyzed enantioselective 1,4-addition of TMSCN to aromatic enones",

abstract = "A facile enantioselective 1,4-addition of TMSCN to aromatic enones has been developed using chiral sodium phosphate. Thus, in the presence of 20 mol% of sodium salt generated in situ from (R)-3,3′-di(1-adamantyl)-1,1′- binaphthyl-2,2′-diylphosphoric acid and NaOH, β-cyano ketones were obtained in high yield (86-96%) and up to 72% ee within three hours at 80 °C in toluene.",

keywords = "1,4-addition, asymmetric catalysis, enones, nitriles, phosphates",

author = "Jingya Yang and Shaoxiang Wu and Chen, {Fu Xue}",

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language = "English",

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journal = "Synlett",

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T1 - Chiral sodium phosphate catalyzed enantioselective 1,4-addition of TMSCN to aromatic enones

AU - Yang, Jingya

AU - Wu, Shaoxiang

AU - Chen, Fu Xue

PY - 2010

Y1 - 2010

N2 - A facile enantioselective 1,4-addition of TMSCN to aromatic enones has been developed using chiral sodium phosphate. Thus, in the presence of 20 mol% of sodium salt generated in situ from (R)-3,3′-di(1-adamantyl)-1,1′- binaphthyl-2,2′-diylphosphoric acid and NaOH, β-cyano ketones were obtained in high yield (86-96%) and up to 72% ee within three hours at 80 °C in toluene.

AB - A facile enantioselective 1,4-addition of TMSCN to aromatic enones has been developed using chiral sodium phosphate. Thus, in the presence of 20 mol% of sodium salt generated in situ from (R)-3,3′-di(1-adamantyl)-1,1′- binaphthyl-2,2′-diylphosphoric acid and NaOH, β-cyano ketones were obtained in high yield (86-96%) and up to 72% ee within three hours at 80 °C in toluene.

KW - 1,4-addition

KW - asymmetric catalysis

KW - enones

KW - nitriles

KW - phosphates

UR - http://www.scopus.com/inward/record.url?scp=78149283092&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1258817

DO - 10.1055/s-0030-1258817

M3 - Article

AN - SCOPUS:78149283092

SN - 0936-5214

SP - 2725

EP - 2728

JO - Synlett

JF - Synlett

IS - 18

ER -

Chiral sodium phosphate catalyzed enantioselective 1,4-addition of TMSCN to aromatic enones

Abstract

Keywords

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