The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids

Michael C. Willis; Gary A. Cutting; Vincent J. D. Piccio; Matthew J. Durbin; Matthew P. John

doi:10.1002/anie.200462125

The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids

Michael C. Willis, Gary A. Cutting, Vincent J. D. Piccio, Matthew J. Durbin, Matthew P. John

Department of Chemistry

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

97 Citations (SciVal)

Abstract

The combination of three reagents-a tridentate pybox ligand (pybox = pyridine bis(oxazoline)), magnesium perchlorate, and Hunig base (iPr 2EtN)-allows the catalytic generation of a chiral glycine enolate from 1 that undergoes highly enantioselective addition to a range of aryl aldehydes 2. The protected aryl β-hydroxy-α-amino acid products obtained include a protected version of one of the aryl serine units present in the glycopeptide antibiotic vancomycin.

Original language	English
Pages (from-to)	1543-1545
Number of pages	3
Journal	Angewandte Chemie International Edition
Volume	44
Issue number	10
DOIs	https://doi.org/10.1002/anie.200462125
Publication status	Published - 2005

Keywords

Synthesis (chemical)
Magnesium printing plates
Amino acids
Antibiotics
Aldehydes
Catalyst activity

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10.1002/anie.200462125

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title = "The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids",

abstract = "The combination of three reagents-a tridentate pybox ligand (pybox = pyridine bis(oxazoline)), magnesium perchlorate, and Hunig base (iPr 2EtN)-allows the catalytic generation of a chiral glycine enolate from 1 that undergoes highly enantioselective addition to a range of aryl aldehydes 2. The protected aryl β-hydroxy-α-amino acid products obtained include a protected version of one of the aryl serine units present in the glycopeptide antibiotic vancomycin.",

keywords = "Synthesis (chemical), Magnesium printing plates, Amino acids, Antibiotics, Aldehydes, Catalyst activity",

author = "Willis, \{Michael C.\} and Cutting, \{Gary A.\} and Piccio, \{Vincent J. D.\} and Durbin, \{Matthew J.\} and John, \{Matthew P.\}",

year = "2005",

doi = "10.1002/anie.200462125",

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pages = "1543--1545",

journal = "Angewandte Chemie International Edition",

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T1 - The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids

AU - Willis, Michael C.

AU - Cutting, Gary A.

AU - Piccio, Vincent J. D.

AU - Durbin, Matthew J.

AU - John, Matthew P.

PY - 2005

Y1 - 2005

N2 - The combination of three reagents-a tridentate pybox ligand (pybox = pyridine bis(oxazoline)), magnesium perchlorate, and Hunig base (iPr 2EtN)-allows the catalytic generation of a chiral glycine enolate from 1 that undergoes highly enantioselective addition to a range of aryl aldehydes 2. The protected aryl β-hydroxy-α-amino acid products obtained include a protected version of one of the aryl serine units present in the glycopeptide antibiotic vancomycin.

AB - The combination of three reagents-a tridentate pybox ligand (pybox = pyridine bis(oxazoline)), magnesium perchlorate, and Hunig base (iPr 2EtN)-allows the catalytic generation of a chiral glycine enolate from 1 that undergoes highly enantioselective addition to a range of aryl aldehydes 2. The protected aryl β-hydroxy-α-amino acid products obtained include a protected version of one of the aryl serine units present in the glycopeptide antibiotic vancomycin.

KW - Synthesis (chemical)

KW - Magnesium printing plates

KW - Amino acids

KW - Antibiotics

KW - Aldehydes

KW - Catalyst activity

UR - http://dx.doi.org/10.1002/anie.200462125

UR - https://www.scopus.com/pages/publications/16244397120

U2 - 10.1002/anie.200462125

DO - 10.1002/anie.200462125

M3 - Article

SN - 1433-7851

VL - 44

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EP - 1545

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 10

ER -

The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids

Abstract

Keywords

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