Abstract
Asymmetric synthesis of (S)-2′,6′-dimethyltyrosine (DMT), (S)-2′,6′-dimethylphenylalanine (DMP), (S)-α,2′,6′-trimethyltyrosine (α-TMT) and (S)-α,2′,6′-trimethylphenylalanine (α-TMP) via reactions of 4′-benzyloxy-2′,6′-dimethylbenzyl bromide or 2′,6′-dimethylbenzylbromide with Ni(II)-complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents, a recyclable chiral auxiliary, simplicity of the experimental procedures and high chemical yields make this method synthetically attractive for preparing the target amino acids on a multi-gram scale.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 6375-6382 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 57 |
| Issue number | 30 |
| DOIs | |
| State | Published - Jul 23 2001 |
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Keywords
- Alkylation reactions
- Amino acids
- Asymmetric synthesis
- Nickel(II) complexes
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Large-scale asymmetric synthesis of novel sterically constrained 2′,6′-dimethyl- and α,2′,6′-trimethyltyrosine and -phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine. / Soloshonok, Vadim A.; Tang, Xuejun; Hruby, Victor J.
In: Tetrahedron, Vol. 57, No. 30, 23.07.2001, p. 6375-6382.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Large-scale asymmetric synthesis of novel sterically constrained 2′,6′-dimethyl- and α,2′,6′-trimethyltyrosine and -phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine
AU - Soloshonok, Vadim A.
AU - Tang, Xuejun
AU - Hruby, Victor J
PY - 2001/7/23
Y1 - 2001/7/23
N2 - Asymmetric synthesis of (S)-2′,6′-dimethyltyrosine (DMT), (S)-2′,6′-dimethylphenylalanine (DMP), (S)-α,2′,6′-trimethyltyrosine (α-TMT) and (S)-α,2′,6′-trimethylphenylalanine (α-TMP) via reactions of 4′-benzyloxy-2′,6′-dimethylbenzyl bromide or 2′,6′-dimethylbenzylbromide with Ni(II)-complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents, a recyclable chiral auxiliary, simplicity of the experimental procedures and high chemical yields make this method synthetically attractive for preparing the target amino acids on a multi-gram scale.
AB - Asymmetric synthesis of (S)-2′,6′-dimethyltyrosine (DMT), (S)-2′,6′-dimethylphenylalanine (DMP), (S)-α,2′,6′-trimethyltyrosine (α-TMT) and (S)-α,2′,6′-trimethylphenylalanine (α-TMP) via reactions of 4′-benzyloxy-2′,6′-dimethylbenzyl bromide or 2′,6′-dimethylbenzylbromide with Ni(II)-complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents, a recyclable chiral auxiliary, simplicity of the experimental procedures and high chemical yields make this method synthetically attractive for preparing the target amino acids on a multi-gram scale.
KW - Alkylation reactions
KW - Amino acids
KW - Asymmetric synthesis
KW - Nickel(II) complexes
UR - http://www.scopus.com/inward/record.url?scp=0035939193&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035939193&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)00504-X
DO - 10.1016/S0040-4020(01)00504-X
M3 - Article
AN - SCOPUS:0035939193
VL - 57
SP - 6375
EP - 6382
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 30
ER -