106872-31-5Relevant articles and documents
Practical syntheses of both enantiomers of cyclopropylglycine and of methyl 2-cyclopropyl-2-N-Boc-iminoacetate
Larionov, Oleg V.,De Meijere, Armin
, p. 1071 - 1078 (2007/10/03)
A facile three-step synthesis of racemic cyclopropylglycine in multigram quantities from inexpensive cyclopropyl methyl ketone has been elaborated. Enzymatic hydrolysis of the N-Boc-protected methyl ester of cyclopropylglycine 9 with the inexpensive enzyme papain from Carica papaya affords both enantiomers of cyclopropylglycine (8) with enantiomeric excesses of 99% or better after deprotection under acidic conditions. Furthermore, the new cyclopropyl group-containing building block methyl 2-cyclopropyl-2-N-Boc-iminoacetate (13) was prepared by N-chlorination and subsequent dehydrochlorination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Addition of nucleophiles to 13 offers a ready access to an unusual, orthogonally bisprotected α,α-diamino acid derivative and interesting components of rigid peptide backbones.
REACTIONS OF AN ELECTROPHILIC GLYCINE CATION EQUIVALENT WITH GRIGNARD REAGENTS A SIMPLE SYNTHESIS OF β,γ-UNSATURATED AMINO ACIDS
Castelhano, Arlindo L.,Horne, Stephen,Billedeau, Roland,Krantz, Allen
, p. 2435 - 2438 (2007/10/02)
A simple and general synthesis of α-amino acids employing vinyl and alkyl Grignard reagents with a glycine cation equivalent is described.
