Some Stereochemical Aspects of the Strecker Synthesis and the Bucherer - Bergs Reaction | Zendy

U.D. Wermuth | Zendy; Ian D. Jenkins | Zendy; R.C. Bott | Zendy; Karl A. Byriel | Zendy; Graham Smith | Zendy

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Some Stereochemical Aspects of the Strecker Synthesis and the Bucherer - Bergs Reaction

Author(s) -

U.D. Wermuth,

Ian D. Jenkins,

R.C. Bott,

Karl A. Byriel,

Graham Smith

Publication year - 2004

Publication title -

australian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.319

H-Index - 77

eISSN - 1445-0038

pISSN - 0004-9425

DOI - 10.1071/ch03202

Subject(s) - strecker amino acid synthesis , chemistry , hydantoin , biocatalysis , bicyclic molecule , heptane , stereochemistry , norbornane , carboxylic acid , hydrolysis , organic chemistry , reaction mechanism , catalysis , enantioselective synthesis

Both the Strecker and Bucherer-Bergs reactions convert the norbornane keto ester methyl bicyclo[2.2.1]hept-6-one-2-endo-carboxylate into the lactam 6-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylic acid-?-lactam-6-exo-carboxylic acid. This lactam is unusually stable and cannot be hydrolyzed to the corresponding amino acid. The stereochemistry in the Strecker reaction, in which the amino group is endo, is contrary to that expected from literature precedent. The stereochemistry in the Bucherer-Bergs reaction, in which the amino group is also endo, has been confirmed by X-ray crystallographic analysis of the intermediate spirohydantoin (ᩭbicyclo[2.2.1]heptane-2-endo-carboxylic acid-6-spiro-5'-hydantoin.Griffith Sciences, School of Natural SciencesFull Tex

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