Trisubstituted 2‑Trifluoromethyl Pyrrolidines via Catalytic Asymmetric Michael Addition/Reductive Cyclization
The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones to nitroolefins proceeds under mild reaction conditions and low catalyst loading...
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| Published in | Organic letters Vol. 16; no. 9; pp. 2362 - 2365 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
02.05.2014
Amer Chemical Soc |
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| Abstract | The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones to nitroolefins proceeds under mild reaction conditions and low catalyst loadings to provide Michael adducts in high yield with excellent diastereo- and enantioselectivity. Catalytic hydrogenation of the Michael adducts stereoselectively generates 2-trifluoromethylated pyrrolidines bearing three contiguous stereocenters. A stereospecific route to epimeric 2-trifluoromethyl pyrrolidines from a common intermediate is described. |
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| AbstractList | The
stereoselective synthesis of trisubstituted 2-trifluoromethyl
pyrrolidines by asymmetric Michael addition/hydrogenative cyclization
is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones
to nitroolefins proceeds under mild reaction conditions and low catalyst
loadings to provide Michael adducts in high yield with excellent diastereo-
and enantioselectivity. Catalytic hydrogenation of the Michael adducts
stereoselectively generates 2-trifluoromethylated pyrrolidines
bearing three contiguous stereocenters. A stereospecific route to
epimeric 2-trifluoromethyl pyrrolidines from a common
intermediate is described. The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones to nitroolefins proceeds under mild reaction conditions and low catalyst loadings to provide Michael adducts in high yield with excellent diastereo- and enantioselectivity. Catalytic hydrogenation of the Michael adducts stereoselectively generates 2-trifluoromethylated pyrrolidines bearing three contiguous stereocenters. A stereospecific route to epimeric 2-trifluoromethyl pyrrolidines from a common intermediate is described. The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones to nitroolefins proceeds under mild reaction conditions and low catalyst loadings to provide Michael adducts in high yield with excellent diastereo- and enantioselectivity. Catalytic hydrogenation of the Michael adducts stereoselectively generates 2-trifluoromethylated pyrrolidines bearing three contiguous stereocenters. A stereospecific route to epimeric 2-trifluoromethyl pyrrolidines from a common intermediate is described. |
| Author | Xu, Qihai Corbett, Michael T. Johnson, Jeffrey S. |
| AuthorAffiliation | Department of Chemistry The University of North Carolina at Chapel Hill |
| AuthorAffiliation_xml | – name: The University of North Carolina at Chapel Hill – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Michael T. surname: Corbett fullname: Corbett, Michael T. – sequence: 2 givenname: Qihai surname: Xu fullname: Xu, Qihai – sequence: 3 givenname: Jeffrey S. surname: Johnson fullname: Johnson, Jeffrey S. email: jsj@unc.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24746344$$D View this record in MEDLINE/PubMed |
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| Keywords | KETONES (S)-ALPHA-TRIFLUOROMETHYL-PROLINE 1,3-DICARBONYL COMPOUNDS ENANTIOSELECTIVE CONJUGATE ADDITION 1,3-DIPOLAR CYCLOADDITION CONSTRUCTION AZOMETHINE YLIDES FLUORINE NITROALKENES TRIFLUOROMETHYLATION |
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| Snippet | The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The... The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The... |
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| SubjectTerms | Catalysis Chemistry Chemistry, Organic Cyclization Hydrocarbons, Fluorinated - chemical synthesis Hydrocarbons, Fluorinated - chemistry Hydrogenation Letter Molecular Structure Physical Sciences Pyrrolidines - chemical synthesis Pyrrolidines - chemistry Science & Technology |
| Title | Trisubstituted 2‑Trifluoromethyl Pyrrolidines via Catalytic Asymmetric Michael Addition/Reductive Cyclization |
| URI | http://dx.doi.org/10.1021/ol500679w http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000335491000017 https://www.ncbi.nlm.nih.gov/pubmed/24746344 https://search.proquest.com/docview/1521336127 https://pubmed.ncbi.nlm.nih.gov/PMC4011570 |
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