Catalytic asymmetric synthesis of glutamate analogues

David J. Burkhart; Andrew R. McKenzie; Jared K. Nelson; Katherine I. Myers; Xue Zhao; Kathy R. Magnusson; Nicholas R. Natale

doi:10.1021/ol049619m

Catalytic asymmetric synthesis of glutamate analogues

David J. Burkhart
, Andrew R. McKenzie
, Jared K. Nelson
, Katherine I. Myers
, Xue Zhao
, Kathy R. Magnusson
, Nicholas R. Natale

University of Idaho

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

15 Scopus citations

Abstract

Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers α or β at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction.

Original language	English
Pages (from-to)	1285-1288
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	8
DOIs	https://doi.org/10.1021/ol049619m
State	Published - Apr 15 2004

Funding

Funder number
R15NS038444

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10.1021/ol049619m

Cite this

@article{0b8cbf4e3fbb43a89aa7763dbb11a7f4,

title = "Catalytic asymmetric synthesis of glutamate analogues",

abstract = "Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers α or β at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction.",

author = "Burkhart, \{David J.\} and McKenzie, \{Andrew R.\} and Nelson, \{Jared K.\} and Myers, \{Katherine I.\} and Xue Zhao and Magnusson, \{Kathy R.\} and Natale, \{Nicholas R.\}",

year = "2004",

month = apr,

day = "15",

doi = "10.1021/ol049619m",

language = "English",

volume = "6",

pages = "1285--1288",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

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TY - JOUR

T1 - Catalytic asymmetric synthesis of glutamate analogues

AU - Burkhart, David J.

AU - McKenzie, Andrew R.

AU - Nelson, Jared K.

AU - Myers, Katherine I.

AU - Zhao, Xue

AU - Magnusson, Kathy R.

AU - Natale, Nicholas R.

PY - 2004/4/15

Y1 - 2004/4/15

N2 - Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers α or β at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction.

AB - Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers α or β at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction.

UR - https://www.scopus.com/pages/publications/2542463908

U2 - 10.1021/ol049619m

DO - 10.1021/ol049619m

M3 - Article

C2 - 15070318

AN - SCOPUS:2542463908

SN - 1523-7060

VL - 6

SP - 1285

EP - 1288

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Catalytic asymmetric synthesis of glutamate analogues

Abstract

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