Diastereoselective cyanation of α-keto amides derived from N-phenyl camphorpyrazolidinone and camphorsultam

Hua Lin Hsu; Hsin Ling Wu; Uppala Venkatesham; Kwun Min Chen

doi:10.1002/jccs.200600058

Diastereoselective cyanation of α-keto amides derived from N-phenyl camphorpyrazolidinone and camphorsultam

Hua Lin Hsu
, Hsin Ling Wu
, Uppala Venkatesham
, Kwun Min Chen^*

^*Corresponding author for this work

Department of Chemistry

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

Abstract

The diastereoselective cyanation of α-keto amides using trimethylsilyl cyanide in the presence of a Lewis acid is described. The corresponding O-acetylated cyanohydrins are obtained in good to high levels of stereoselectivities. The predominance of products with the S absolute configuration at the newly generated stereogenic center was deduced from single crystal X-ray analysis. ¹³C NMR data suggest that a preferential s-cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.

Original language	English
Pages (from-to)	448-454
Number of pages	7
Journal	Journal of the Chinese Chemical Society
Volume	53
Issue number	2
DOIs	https://doi.org/10.1002/jccs.200600058
Publication status	Published - 2006 Apr

Keywords

Chiral auxiliary
Cyanation
Diastereoselective
Lewis acid
Timethylsilyl cyanide
α-ketoamides

ASJC Scopus subject areas

General Chemistry

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10.1002/jccs.200600058

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abstract = "The diastereoselective cyanation of α-keto amides using trimethylsilyl cyanide in the presence of a Lewis acid is described. The corresponding O-acetylated cyanohydrins are obtained in good to high levels of stereoselectivities. The predominance of products with the S absolute configuration at the newly generated stereogenic center was deduced from single crystal X-ray analysis. 13C NMR data suggest that a preferential s-cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.",

keywords = "Chiral auxiliary, Cyanation, Diastereoselective, Lewis acid, Timethylsilyl cyanide, α-ketoamides",

author = "Hsu, \{Hua Lin\} and Wu, \{Hsin Ling\} and Uppala Venkatesham and Chen, \{Kwun Min\}",

year = "2006",

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language = "English",

volume = "53",

pages = "448--454",

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AU - Hsu, Hua Lin

AU - Wu, Hsin Ling

AU - Venkatesham, Uppala

AU - Chen, Kwun Min

PY - 2006/4

Y1 - 2006/4

N2 - The diastereoselective cyanation of α-keto amides using trimethylsilyl cyanide in the presence of a Lewis acid is described. The corresponding O-acetylated cyanohydrins are obtained in good to high levels of stereoselectivities. The predominance of products with the S absolute configuration at the newly generated stereogenic center was deduced from single crystal X-ray analysis. 13C NMR data suggest that a preferential s-cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.

AB - The diastereoselective cyanation of α-keto amides using trimethylsilyl cyanide in the presence of a Lewis acid is described. The corresponding O-acetylated cyanohydrins are obtained in good to high levels of stereoselectivities. The predominance of products with the S absolute configuration at the newly generated stereogenic center was deduced from single crystal X-ray analysis. 13C NMR data suggest that a preferential s-cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.

KW - Chiral auxiliary

KW - Cyanation

KW - Diastereoselective

KW - Lewis acid

KW - Timethylsilyl cyanide

KW - α-ketoamides

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M3 - Article

AN - SCOPUS:34047110190

SN - 0009-4536

VL - 53

SP - 448

EP - 454

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

IS - 2

ER -

Diastereoselective cyanation of α-keto amides derived from N-phenyl camphorpyrazolidinone and camphorsultam

Abstract

Keywords

ASJC Scopus subject areas

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