Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones

Jacqueline H. Smitrovich; Geneviève N. Boice; Chuanxing Qu; Lisa DiMichele; Todd D. Nelson; Mark A. Huffman; Jerry Murry; James McNamara; Paul J. Reider

doi:10.1021/ol0259847

Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones

Jacqueline H. Smitrovich, Geneviève N. Boice, Chuanxing Qu, Lisa DiMichele, Todd D. Nelson, Mark A. Huffman, Jerry Murry, James McNamara, Paul J. Reider

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

32 Scopus citations

Abstract

(Equation Presented) The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-δ-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted δ-lactones.

Original language	English (US)
Pages (from-to)	1963-1966
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	11
DOIs	https://doi.org/10.1021/ol0259847
State	Published - May 30 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0259847

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title = "Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones",

abstract = "(Equation Presented) The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-δ-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted δ-lactones.",

author = "Smitrovich, {Jacqueline H.} and Boice, {Genevi{\`e}ve N.} and Chuanxing Qu and Lisa DiMichele and Nelson, {Todd D.} and Huffman, {Mark A.} and Jerry Murry and James McNamara and Reider, {Paul J.}",

year = "2002",

month = may,

day = "30",

doi = "10.1021/ol0259847",

language = "English (US)",

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pages = "1963--1966",

journal = "Organic Letters",

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T1 - Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions

T2 - Synthesis of 3-Aryl-δ-lactones

AU - Smitrovich, Jacqueline H.

AU - Boice, Geneviève N.

AU - Qu, Chuanxing

AU - DiMichele, Lisa

AU - Nelson, Todd D.

AU - Huffman, Mark A.

AU - Murry, Jerry

AU - McNamara, James

AU - Reider, Paul J.

PY - 2002/5/30

Y1 - 2002/5/30

N2 - (Equation Presented) The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-δ-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted δ-lactones.

AB - (Equation Presented) The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-δ-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted δ-lactones.

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U2 - 10.1021/ol0259847

DO - 10.1021/ol0259847

M3 - Article

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VL - 4

SP - 1963

EP - 1966

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones

Abstract

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