Enantioselective Catalyst Systems from Copper(II) Triflate and BINOL–Silanediol
Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle functionalization. The promise of this silanediol and copper catalyst combination is demonstrated in the enantioselective addition of indoles to alkyliden...
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| Published in | Chemistry : a European journal Vol. 24; no. 28; pp. 7123 - 7127 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
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17.05.2018
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| Abstract | Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle functionalization. The promise of this silanediol and copper catalyst combination is demonstrated in the enantioselective addition of indoles to alkylidene malonates to give rise to the desirable adducts in excellent yield and high enantiomeric excess. From these studies, 1,1′‐bi‐2‐naphthol (BINOL)‐based silanediols emerge as one‐of‐a‐kind cocatalysts. Their potential role in the reaction pathway is also discussed.
Better together: Silanediol and copper(II) triflate work together to create an enhanced catalyst system for enantioselective heterocycle functionalization. This unique catalyst combination activates alkylidene malonates for reaction with indoles to give rise to desirable products in excellent yield and high levels of enantiomeric excess (see figure). |
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| AbstractList | Abstract
Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle functionalization. The promise of this silanediol and copper catalyst combination is demonstrated in the enantioselective addition of indoles to alkylidene malonates to give rise to the desirable adducts in excellent yield and high enantiomeric excess. From these studies, 1,1′‐bi‐2‐naphthol (BINOL)‐based silanediols emerge as one‐of‐a‐kind cocatalysts. Their potential role in the reaction pathway is also discussed. Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle functionalization. The promise of this silanediol and copper catalyst combination is demonstrated in the enantioselective addition of indoles to alkylidene malonates to give rise to the desirable adducts in excellent yield and high enantiomeric excess. From these studies, 1,1'-bi-2-naphthol (BINOL)-based silanediols emerge as one-of-a-kind cocatalysts. Their potential role in the reaction pathway is also discussed. Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle functionalization. The promise of this silanediol and copper catalyst combination is demonstrated in the enantioselective addition of indoles to alkylidene malonates to give rise to the desirable adducts in excellent yield and high enantiomeric excess. From these studies, 1,1′‐bi‐2‐naphthol (BINOL)‐based silanediols emerge as one‐of‐a‐kind cocatalysts. Their potential role in the reaction pathway is also discussed. Better together: Silanediol and copper(II) triflate work together to create an enhanced catalyst system for enantioselective heterocycle functionalization. This unique catalyst combination activates alkylidene malonates for reaction with indoles to give rise to desirable products in excellent yield and high levels of enantiomeric excess (see figure). |
| Author | Guan, Yong Mattson, Anita E. Attard, Jonathan W. Fisher, Thomas J. Visco, Michael D. |
| AuthorAffiliation | [a] Department of Chemistry and Biochemistry Worcester Polytechnic Institute, 100 Institute Road, Worcester, MA 01609 (USA) [b] Celgene, 86 Morris Avenue, Summit, NJ (USA) [c] The Goodyear Tire and Rubber Company, 200 Innovation Way, Akron, OH (USA) |
| AuthorAffiliation_xml | – name: [c] The Goodyear Tire and Rubber Company, 200 Innovation Way, Akron, OH (USA) – name: [a] Department of Chemistry and Biochemistry Worcester Polytechnic Institute, 100 Institute Road, Worcester, MA 01609 (USA) – name: [b] Celgene, 86 Morris Avenue, Summit, NJ (USA) |
| Author_xml | – sequence: 1 givenname: Yong surname: Guan fullname: Guan, Yong organization: Worcester Polytechnic Institute – sequence: 2 givenname: Jonathan W. surname: Attard fullname: Attard, Jonathan W. organization: Worcester Polytechnic Institute – sequence: 3 givenname: Michael D. surname: Visco fullname: Visco, Michael D. organization: Celgene – sequence: 4 givenname: Thomas J. surname: Fisher fullname: Fisher, Thomas J. organization: The Goodyear Tire and Rubber Company – sequence: 5 givenname: Anita E. orcidid: 0000-0003-4662-3468 surname: Mattson fullname: Mattson, Anita E. email: aemattson@wpi.edu organization: Worcester Polytechnic Institute |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29575279$$D View this record in MEDLINE/PubMed |
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| Keywords | enantioselectivity Friedel-Crafts reactions ACIDS cooperative catalysis copper silanediols ANION RECOGNITION FRIEDEL-CRAFTS ALKYLATION PROTEASE INHIBITORS INDOLES |
| Language | English |
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| Notes | These authors contributed equally to this work. BINOL=1,1′‐bi‐2‐naphthol. NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Snippet | Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle... Abstract Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle... |
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| SubjectTerms | Adducts Alkylidene Catalysis Catalysts Chemistry Chemistry, Multidisciplinary cooperative catalysis Copper Copper compounds Enantiomers enantioselectivity Friedel–Crafts reactions Indoles Lewis acid Naphthol Physical Sciences Science & Technology silanediols |
| Title | Enantioselective Catalyst Systems from Copper(II) Triflate and BINOL–Silanediol |
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