Zinc mediated addition of active halides to a glycine cation equivalent: Synthesis of N-Boc-L-propargylglycine

The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with α-chymotrypsin affords N-Boc-L-propargylgl...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 22; pp. 3669 - 3672
Main Authors Abood, Norman A, Nosal, Roger
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.05.1994
Elsevier
Subjects
Aliphatic compounds
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ALPHA-AMINO-ACIDS
ASYMMETRIC-SYNTHESIS
DERIVATIVES
GRIGNARD-REAGENTS
ESTERS
Alkynylation
α-Aminoacid
Acetylenic compound
Aliphatic compound
Optical resolution
Enzymatic catalysis
Alkylation
Zinc
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Summary:The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with α-chymotrypsin affords N-Boc-L-propargylglycine in 99% e.e.. Reaction of methyl N-Boc-2-acetoxyglycine with propargyl bromide and Zn dust followed by kinetic resolution with α-chymotropsin affords N-Boc-L-propargylglycine in good yield (99%e.e.).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)73067-X