+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Allylic halogenation of unsaturated amino acids

Allylic halogenation of unsaturated amino acids

Organic and Biomolecular Chemistry 1(14): 2492-2498

A range of dehydro amino acid derivatives has been prepared and subjected to halogenation using either molecular bromine or chlorine, or NBS. Allylic halogenation of the unsaturated amino acid side chains occurs through radical bromination with NBS. The procedure is complementary to treatment with chlorine, which also affords allyl halides. This latter and unusual reaction is shown through a deuterium labelling study to proceed via an ionic mechanism. The choice of NBS or chlorine for allyl halide synthesis is shown to depend on the potential to avoid competing reactions, such as halolactonization of leucine derivatives with chlorine, and hydrogen abstraction and bromine incorporation at multiple sites on treatment of isoleucine derivatives with NBS. The synthetic utility of the allyl halides prepared in this study is indicated through the synthesis of a cyclopropyl amino acid derivative and the extension of the carbon skeleton of an amino acid side chain.

Please choose payment method:

(PDF emailed within 1 workday: $29.90)

Accession: 048210964

Download citation: RISBibTeXText

PMID: 12956066

Related references

Pd-Catalyzed Stereodivergent Allylic Amination of α-Tertiary Allylic Alcohols towards α,β-Unsaturated γ-Amino Acids. Chemsuschem 12(13): 3152-3158, 2019

Allylic halogenation and oxidation of long chain alpha,beta unsaturated ester. Journal of the American Oil Chemists' Society: 55 (5) 491-495, 1978

Synthesis ofγ,δ-unsaturated amino acids via ester enolate Claisen rearrangement of chelated allylic esters. Amino Acids 11(3-4): 283-299, 1996

Synthesis of gamma,delta-unsaturated amino acids via ester enolate Claisen rearrangement of chelated allylic esters. Amino Acids 11(3-4): 283-299, 1996

Stereocontrolled synthesis of R or S, E or Z unsaturated alpha-amino acids by enantio- and diastereoselective epoxidation of delta-hydroxy allylic phosphine oxides. Tetrahedron Letters 34(8): 1327-1330, 1993

Studies on iodine number. I. Mechanisms of halogenation of unsaturated fatty acids. Roczniki Panstwowego Zakladu Higieny 18(1): 23-29, 1967

Polyenolates of unsaturated carboxylic acids in synthesis synthesis of unsaturated alpha amino acids and gamma hydrazino acids. Synthetic Communications 21(18-19): 1833-1840, 1991

Umpolung in allylic phosphonates regio selective and stereo selective synthesis of e gamma amino alpha beta unsaturated phosphonates by palladium catalyzed reaction of allylic acetoxy phosphonates. Journal of the Chemical Society Chemical Communications (17): 1318-1319, 1987

Unsaturated Amino Alcohols via Cyclization of Allylic Bistrichloroacetimidates. Synlett 24(18): 2345-2349, 2013

Halogenation and acyloxylation of n cyclohex 2 en 1 on 3 yl amino acids. Zeitschrift fuer Naturforschung Section B Chemical Sciences 46(10): 1415-1420, 1991

Synthesis of nonproteinogenic amino acids part 3. conversion of glutamic acid into gamma delta unsaturated alpha amino acids. Tetrahedron 45(5): 1465-1474, 1989

Synthesis of ω-Oxo Amino Acids and trans-5-Substituted Proline Derivatives Using Cross-Metathesis of Unsaturated Amino Acids. Journal of Organic Chemistry 81(18): 8386-8393, 2016

Stereocontrolled Synthesis of Quaternary β,γ-Unsaturated Amino Acids: Chain Extension of D- & L- α-(2-Tributylstannyl)Vinyl Amino Acids. Tetrahedron 57(30): 6329-6343, 2001

Photochemical activation of amino acids: From the synthesis of enantiomerically pure beta,gamma-unsaturated amino acids to macrocyclic ring systems. Liebigs Annalen 0(12): 1951-1958, 1996

Polyenolates of Unsaturated Carboxylic Acids in Synthesis. Synthesis of Unsaturated α-Amino Acids and β-Hydrazing Acids. Synthetic Communications 21(18-19): 1833-1839, 1991