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Diastereoselective Cyanation of α‐Keto Amides Derived from N ‐Phenyl Camphorpyrazolidinone and Camphorsultam
Author(s) -
Hsu HuaLin,
Wu HsinLing,
Venkatesham Uppala,
Chen KwunMin
Publication year - 2006
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200600058
Subject(s) - chemistry , cyanation , stereocenter , lewis acids and bases , trimethylsilyl cyanide , cyanide , chelation , stereochemistry , trimethylsilyl , medicinal chemistry , oxygen atom , organic chemistry , catalysis , molecule , enantioselective synthesis
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. 13 C NMR data suggest that a preferential s‐cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.