Diastereoselective and Enantioselective Synthesis of α-p-Methoxyphenoxy-β-Lactones : Dependence on the Stereoelectronic Properties of the β-Hydroxy-α-p-Methoxyphenoxycarboxylic Acid Precursors
Treatment of β-hydroxy-α-p-methoxyphenoxy carboxylic acids derived from the asymmetric glycolate aldol addition reaction with p-nitrobenzenesulfonyl chloride yielded divergent results depending on the nature of the β-substituent of the carboxylic acid. Substrates bearing either alkyl substituents (R = -n-butyl, -n-octyl, -benzyl, isopropyl, -tert-butyl) or aryl systems bearing electron-withdrawing substituents (R = -p-C6H4Cl, -p-C6H4Br, -p-C6H4NO2) yielded β-lactones. In contrast, α-p-methoxyphenoxy-β-hydroxycarboxylic acids bearing electron-donating aryl groups or the sterically demanding 2-naphthyl group formed (Z)-alkenes.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2022 |
|---|---|
| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:87 |
|---|---|
| Enthalten in: |
The Journal of organic chemistry - 87(2022), 15 vom: 05. Aug., Seite 9619-9634 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Witte, Jordan M [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Alkenes |
|---|
| Anmerkungen: |
Date Completed 09.08.2022 Date Revised 19.09.2022 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1021/acs.joc.2c00608 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM343825201 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM343825201 | ||
| 003 | DE-627 | ||
| 005 | 20231226021343.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231226s2022 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.joc.2c00608 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1146.xml |
| 035 | |a (DE-627)NLM343825201 | ||
| 035 | |a (NLM)35862509 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Witte, Jordan M |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Diastereoselective and Enantioselective Synthesis of α-p-Methoxyphenoxy-β-Lactones |b Dependence on the Stereoelectronic Properties of the β-Hydroxy-α-p-Methoxyphenoxycarboxylic Acid Precursors |
| 264 | 1 | |c 2022 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 09.08.2022 | ||
| 500 | |a Date Revised 19.09.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Treatment of β-hydroxy-α-p-methoxyphenoxy carboxylic acids derived from the asymmetric glycolate aldol addition reaction with p-nitrobenzenesulfonyl chloride yielded divergent results depending on the nature of the β-substituent of the carboxylic acid. Substrates bearing either alkyl substituents (R = -n-butyl, -n-octyl, -benzyl, isopropyl, -tert-butyl) or aryl systems bearing electron-withdrawing substituents (R = -p-C6H4Cl, -p-C6H4Br, -p-C6H4NO2) yielded β-lactones. In contrast, α-p-methoxyphenoxy-β-hydroxycarboxylic acids bearing electron-donating aryl groups or the sterically demanding 2-naphthyl group formed (Z)-alkenes | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Alkenes |2 NLM | |
| 650 | 7 | |a Hydroxy Acids |2 NLM | |
| 650 | 7 | |a Lactones |2 NLM | |
| 700 | 1 | |a Service, Jasmine |e verfasserin |4 aut | |
| 700 | 1 | |a Addo, Marian Aba |e verfasserin |4 aut | |
| 700 | 1 | |a Semakieh, Bader |e verfasserin |4 aut | |
| 700 | 1 | |a Collins, Erin |e verfasserin |4 aut | |
| 700 | 1 | |a Sams, Christopher |e verfasserin |4 aut | |
| 700 | 1 | |a Dorsey, Timothy R |e verfasserin |4 aut | |
| 700 | 1 | |a Garrelts, Elizabeth |e verfasserin |4 aut | |
| 700 | 1 | |a Blumenshine, Cassidy A |e verfasserin |4 aut | |
| 700 | 1 | |a Cooper, Trace |e verfasserin |4 aut | |
| 700 | 1 | |a Martinez, Moses |e verfasserin |4 aut | |
| 700 | 1 | |a Hamaker, Christopher G |e verfasserin |4 aut | |
| 700 | 1 | |a Ferrence, Gregory M |e verfasserin |4 aut | |
| 700 | 1 | |a Hitchcock, Shawn R |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t The Journal of organic chemistry |d 1945 |g 87(2022), 15 vom: 05. Aug., Seite 9619-9634 |w (DE-627)NLM000006343 |x 1520-6904 |7 nnns |
| 773 | 1 | 8 | |g volume:87 |g year:2022 |g number:15 |g day:05 |g month:08 |g pages:9619-9634 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.joc.2c00608 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 87 |j 2022 |e 15 |b 05 |c 08 |h 9619-9634 | ||