Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation

Michael T. Crimmins; Kyle A. Emmitte; Jason D. Katz

doi:10.1021/ol006091m

Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation

Michael T. Crimmins, Kyle A. Emmitte, Jason D. Katz

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111 Scopus citations

Abstract

matrix presented The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of α-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols. Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation. Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.

Original language	English
Pages (from-to)	2165-2167
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	14
DOIs	https://doi.org/10.1021/ol006091m
State	Published - 13 Jul 2000

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title = "Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation",

abstract = "matrix presented The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of α-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols. Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation. Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.",

author = "Crimmins, {Michael T.} and Emmitte, {Kyle A.} and Katz, {Jason D.}",

year = "2000",

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doi = "10.1021/ol006091m",

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journal = "Organic Letters",

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T1 - Diastereoselective alkylations of oxazolidinone glycolates

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AU - Crimmins, Michael T.

AU - Emmitte, Kyle A.

AU - Katz, Jason D.

PY - 2000/7/13

Y1 - 2000/7/13

N2 - matrix presented The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of α-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols. Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation. Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.

AB - matrix presented The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of α-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols. Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation. Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.

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U2 - 10.1021/ol006091m

DO - 10.1021/ol006091m

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JO - Organic Letters

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ER -

Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation

Abstract

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