A photochemical approach to phenylalanines and related compounds by alkylation of glycine

H S  Knowles; K  Hunt; A F  Parsons

A photochemical approach to phenylalanines and related compounds by alkylation of glycine

H S Knowles, K Hunt, A F Parsons

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Phenylalanines can be prepared on UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, substituted toluenes and the photosensitiser benzophenone. These reactions, which lead to highly selective mono-alkylation at the alpha -position of glycines, involve coupling of captodative alpha -glycine radicals with benzyl radicals. This method can be used to selectively alkylate a variety of glycine derivatives using a range of substituted toluenes under neutral reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	8115-8124
Number of pages	10
Journal	Tetrahedron
Volume	57
Issue number	38
Publication status	Published - 17 Sept 2001

Keywords

alkylation
amino acids and derivatives
photochemistry
radicals and radical reactions
ALPHA-AMINO-ACIDS
FREE-RADICAL REACTIONS
ASYMMETRIC-SYNTHESIS
DERIVATIVES
PHOTOALKYLATION
DESULFONYLATION
HYDROGENATION
CATALYSTS
RESIDUES
ALCOHOLS

Cite this

@article{570cd3fe6cd74176b7c5104ad004bf0f,

title = "A photochemical approach to phenylalanines and related compounds by alkylation of glycine",

abstract = "Phenylalanines can be prepared on UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, substituted toluenes and the photosensitiser benzophenone. These reactions, which lead to highly selective mono-alkylation at the alpha -position of glycines, involve coupling of captodative alpha -glycine radicals with benzyl radicals. This method can be used to selectively alkylate a variety of glycine derivatives using a range of substituted toluenes under neutral reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "alkylation, amino acids and derivatives, photochemistry, radicals and radical reactions, ALPHA-AMINO-ACIDS, FREE-RADICAL REACTIONS, ASYMMETRIC-SYNTHESIS, DERIVATIVES, PHOTOALKYLATION, DESULFONYLATION, HYDROGENATION, CATALYSTS, RESIDUES, ALCOHOLS",

author = "Knowles, {H S} and K Hunt and Parsons, {A F}",

year = "2001",

month = sep,

day = "17",

language = "English",

volume = "57",

pages = "8115--8124",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "38",

}

TY - JOUR

T1 - A photochemical approach to phenylalanines and related compounds by alkylation of glycine

AU - Knowles, H S

AU - Hunt, K

AU - Parsons, A F

PY - 2001/9/17

Y1 - 2001/9/17

N2 - Phenylalanines can be prepared on UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, substituted toluenes and the photosensitiser benzophenone. These reactions, which lead to highly selective mono-alkylation at the alpha -position of glycines, involve coupling of captodative alpha -glycine radicals with benzyl radicals. This method can be used to selectively alkylate a variety of glycine derivatives using a range of substituted toluenes under neutral reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - Phenylalanines can be prepared on UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, substituted toluenes and the photosensitiser benzophenone. These reactions, which lead to highly selective mono-alkylation at the alpha -position of glycines, involve coupling of captodative alpha -glycine radicals with benzyl radicals. This method can be used to selectively alkylate a variety of glycine derivatives using a range of substituted toluenes under neutral reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - alkylation

KW - amino acids and derivatives

KW - photochemistry

KW - radicals and radical reactions

KW - ALPHA-AMINO-ACIDS

KW - FREE-RADICAL REACTIONS

KW - ASYMMETRIC-SYNTHESIS

KW - DERIVATIVES

KW - PHOTOALKYLATION

KW - DESULFONYLATION

KW - HYDROGENATION

KW - CATALYSTS

KW - RESIDUES

KW - ALCOHOLS

M3 - Article

SN - 0040-4020

VL - 57

SP - 8115

EP - 8124

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -