Tertiary α‐Silyl Alcohols by Diastereoselective Coupling of 1,3‐Dienes and Acylsilanes Initiated by Enantioselective Copper‐Catalyzed Borylation
An efficient synthesis of functionalized tertiary α‐silyl alcohols by an enantio‐ and diastereoselective copper‐catalyzed three‐component coupling of 1,3‐dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3‐dienes and a broad range of aryl‐ as we...
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| Published in | Angewandte Chemie International Edition Vol. 58; no. 24; pp. 8211 - 8215 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
11.06.2019
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | An efficient synthesis of functionalized tertiary α‐silyl alcohols by an enantio‐ and diastereoselective copper‐catalyzed three‐component coupling of 1,3‐dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3‐dienes and a broad range of aryl‐ as well as alkenyl‐ but also alkyl‐substituted acylsilanes. The target compounds are formed with high regio‐, diastereo‐, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks.
All at once: A copper‐catalyzed three‐component coupling of 1,3‐dienes, bis(pinacolato)diboron, and acylsilanes affords densely functionalized tertiary α‐silyl alcohols regioselectively in high yields as well as with excellent enantioselectivity (up to 99 % ee) and diastereoselectivity (d.r. >20:1). Subsequent transformations illustrate the versatility of these chiral building blocks. |
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| AbstractList | An efficient synthesis of functionalized tertiary α‐silyl alcohols by an enantio‐ and diastereoselective copper‐catalyzed three‐component coupling of 1,3‐dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3‐dienes and a broad range of aryl‐ as well as alkenyl‐ but also alkyl‐substituted acylsilanes. The target compounds are formed with high regio‐, diastereo‐, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks.
All at once: A copper‐catalyzed three‐component coupling of 1,3‐dienes, bis(pinacolato)diboron, and acylsilanes affords densely functionalized tertiary α‐silyl alcohols regioselectively in high yields as well as with excellent enantioselectivity (up to 99 % ee) and diastereoselectivity (d.r. >20:1). Subsequent transformations illustrate the versatility of these chiral building blocks. An efficient synthesis of functionalized tertiary α‐silyl alcohols by an enantio‐ and diastereoselective copper‐catalyzed three‐component coupling of 1,3‐dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3‐dienes and a broad range of aryl‐ as well as alkenyl‐ but also alkyl‐substituted acylsilanes. The target compounds are formed with high regio‐, diastereo‐, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks. An efficient synthesis of functionalized tertiary α‐silyl alcohols by an enantio‐ and diastereoselective copper‐catalyzed three‐component coupling of 1,3‐dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3‐dienes and a broad range of aryl‐ as well as alkenyl‐ but also alkyl‐substituted acylsilanes. The target compounds are formed with high regio‐, diastereo‐, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks. An efficient synthesis of functionalized tertiary alpha-silyl alcohols by an enantio- and diastereoselective copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3-dienes and a broad range of aryl- as well as alkenyl- but also alkyl-substituted acylsilanes. The target compounds are formed with high regio-, diastereo-, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks. An efficient synthesis of functionalized tertiary α-silyl alcohols by an enantio- and diastereoselective copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3-dienes and a broad range of aryl- as well as alkenyl- but also alkyl-substituted acylsilanes. The target compounds are formed with high regio-, diastereo-, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks.An efficient synthesis of functionalized tertiary α-silyl alcohols by an enantio- and diastereoselective copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3-dienes and a broad range of aryl- as well as alkenyl- but also alkyl-substituted acylsilanes. The target compounds are formed with high regio-, diastereo-, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks. |
| Author | Feng, Jian‐Jun Oestreich, Martin |
| Author_xml | – sequence: 1 givenname: Jian‐Jun orcidid: 0000-0002-6094-3268 surname: Feng fullname: Feng, Jian‐Jun organization: Technische Universität Berlin – sequence: 2 givenname: Martin orcidid: 0000-0002-1487-9218 surname: Oestreich fullname: Oestreich, Martin email: martin.oestreich@tu-berlin.de organization: Technische Universität Berlin |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30947388$$D View this record in MEDLINE/PubMed |
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| Keywords | multicomponent reactions BOND FORMATION asymmetric catalysis ARYLBORATION ALLENES BROOK REARRANGEMENT silicon BIS(PINACOLATO)DIBORON ALDOL REACTION copper GENERATION 2 STEREOCENTERS ADDITIONS boron IN-SITU |
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| SubjectTerms | Alcohol Alcohols Aromatic compounds asymmetric catalysis boron Chemical synthesis Chemistry Chemistry, Multidisciplinary Copper Coupling Dienes Enantiomers multicomponent reactions Physical Sciences Science & Technology silicon Stereoselectivity |
| Title | Tertiary α‐Silyl Alcohols by Diastereoselective Coupling of 1,3‐Dienes and Acylsilanes Initiated by Enantioselective Copper‐Catalyzed Borylation |
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