Asymmetric dihydroxylations of enynes with a trisubstituted C═C bond. An unprecedented route to γ-lactone building blocks with a quaternary stereocenter
En route to a comprehensive set of hydroxylactone building blocks (4R,5R)-, (4R,5S)-, (4S,5R)-, and (4S,5S)-5a, Sharpless asymmetric dihydroxylations of allylic chlorides (E)- and (Z)-9 were performed. They delivered the four stereoisomers of diol 10 with up to 92% ee and absolute configurations, which were proven to be in accordance with the Sharpless mnemonic.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2011 |
|---|---|
| Erschienen: |
2011 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:13 |
|---|---|
| Enthalten in: |
Organic letters - 13(2011), 5 vom: 04. März, Seite 1016-9 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Burghart-Stoll, Heike [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Alcohols |
|---|
| Anmerkungen: |
Date Completed 06.05.2011 Date Revised 25.02.2011 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1021/ol103061g |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM205398944 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM205398944 | ||
| 003 | DE-627 | ||
| 005 | 20231223233855.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231223s2011 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/ol103061g |2 doi | |
| 028 | 5 | 2 | |a pubmed24n0685.xml |
| 035 | |a (DE-627)NLM205398944 | ||
| 035 | |a (NLM)21271731 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Burghart-Stoll, Heike |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Asymmetric dihydroxylations of enynes with a trisubstituted C═C bond. An unprecedented route to γ-lactone building blocks with a quaternary stereocenter |
| 264 | 1 | |c 2011 | |
| 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 06.05.2011 | ||
| 500 | |a Date Revised 25.02.2011 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a En route to a comprehensive set of hydroxylactone building blocks (4R,5R)-, (4R,5S)-, (4S,5R)-, and (4S,5S)-5a, Sharpless asymmetric dihydroxylations of allylic chlorides (E)- and (Z)-9 were performed. They delivered the four stereoisomers of diol 10 with up to 92% ee and absolute configurations, which were proven to be in accordance with the Sharpless mnemonic | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Alcohols |2 NLM | |
| 650 | 7 | |a Alkenes |2 NLM | |
| 650 | 7 | |a Alkynes |2 NLM | |
| 650 | 7 | |a Hydrocarbons, Chlorinated |2 NLM | |
| 650 | 7 | |a Lactones |2 NLM | |
| 700 | 1 | |a Kapferer, Tobias |e verfasserin |4 aut | |
| 700 | 1 | |a Brückner, Reinhard |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic letters |d 1999 |g 13(2011), 5 vom: 04. März, Seite 1016-9 |w (DE-627)NLM106817639 |x 1523-7052 |7 nnns |
| 773 | 1 | 8 | |g volume:13 |g year:2011 |g number:5 |g day:04 |g month:03 |g pages:1016-9 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/ol103061g |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 13 |j 2011 |e 5 |b 04 |c 03 |h 1016-9 | ||