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Syntheses and Reactions of 1‐Amino‐2,2‐dialkylcyclopropane‐1‐carbonitriles and ‐carboxamides – Potential Precursors of ACC Derivatives
Author(s) -
Aelterman Wim,
Tehrani Kourosch Abbaspour,
Coppens Wim,
Huybrechts Tom,
De Kimpe Norbert,
Tourwé Dirk,
Declercq JeanPaul
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199901)1999:1<239::aid-ejoc239>3.0.co;2-z
Subject(s) - chemistry , potassium cyanide , potassium , cyanide , strecker amino acid synthesis , stereochemistry , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis
The direct cyclization of 2‐amino‐4‐chloro‐3,3‐dimethylbutanenitrile with potassium tert ‐butoxide in THF afforded 1‐amino‐2,2‐dimethylcyclopropane‐1‐carbonitrile and a dimerization product. Various new cis ‐ and trans ‐1‐( tert‐ butylamino)‐2‐benzyl‐2‐methylcyclopropane‐carbonitriles and© the corresponding cyclopropanecarboxamides have been synthesized, with focus on the isolation of the pure stereoisomeric cyclopropanecarboxamides. The relative configuration of the stereoisomers was established by X‐ray crystallographic analysis of one of the model compounds. A new route to the latter functionalized cyclopropanes was developed by reaction of 1‐methoxycyclopropylamines with potassium cyanide. Some remarkable rearrangements of 1‐aminocyclopropane‐1‐carbonitriles into azetidine and oxazine derivatives via Favorskii‐derived intermediates are reported. Various aspects of the chemistry of geminally functionalized cyclopropanes are discussed.