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

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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",

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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 - http://www.scopus.com/inward/record.url?scp=2542463908&partnerID=8YFLogxK

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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