A Robust, Efficient, and Highly Enantioselective Method for Synthesis of Homopropargyl Amines
Fast, robust, selective: Copper‐catalyzed enantioselective additions of homopropargyl groups to a wide range of aldimines proceed readily and with high enantioselectivity. The catalytic method is scalable and practical, the allenylboron reagent is commercially available, and conversion into amines i...
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| Published in: | Angewandte Chemie International Edition Vol. 51; no. 27; pp. 6618 - 6621 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Weinheim
WILEY-VCH Verlag
02-07-2012
WILEY‐VCH Verlag |
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| Abstract | Fast, robust, selective: Copper‐catalyzed enantioselective additions of homopropargyl groups to a wide range of aldimines proceed readily and with high enantioselectivity. The catalytic method is scalable and practical, the allenylboron reagent is commercially available, and conversion into amines is inexpensive and high‐yielding. |
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| AbstractList | Fast, robust, selective: Copper‐catalyzed enantioselective additions of homopropargyl groups to a wide range of aldimines proceed readily and with high enantioselectivity. The catalytic method is scalable and practical, the allenylboron reagent is commercially available, and conversion into amines is inexpensive and high‐yielding. |
| Author | Haeffner, Fredrik Vieira, Erika M. Hoveyda, Amir H. Snapper, Marc L. |
| Author_xml | – sequence: 1 givenname: Erika M. surname: Vieira fullname: Vieira, Erika M. organization: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA) – sequence: 2 givenname: Fredrik surname: Haeffner fullname: Haeffner, Fredrik organization: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA) – sequence: 3 givenname: Marc L. surname: Snapper fullname: Snapper, Marc L. organization: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA) – sequence: 4 givenname: Amir H. surname: Hoveyda fullname: Hoveyda, Amir H. email: amir.hoveyda@bc.edu organization: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22623437$$D View this record in MEDLINE/PubMed |
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| ContentType | Journal Article |
| Copyright | Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2012 |
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| Notes | ArticleID:ANIE201202694 NIH - No. GM-57212 istex:33213DE11FD5BA1230A9FC4E662A5E31CAA8ADD2 Financial support was provided by the NIH (GM-57212). We are grateful to Dr. B. Li for securing X-ray structures and to Frontier Scientific, Inc. for gifts of the allenylboron reagent. We thank Boston College Research Services for providing access to computational facilities. ark:/67375/WNG-6Q0SCQ19-L Financial support was provided by the NIH (GM‐57212). We are grateful to Dr. B. Li for securing X‐ray structures and to Frontier Scientific, Inc. for gifts of the allenylboron reagent. We thank Boston College Research Services for providing access to computational facilities. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Snippet | Fast, robust, selective: Copper‐catalyzed enantioselective additions of homopropargyl groups to a wide range of aldimines proceed readily and with high... |
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| SubjectTerms | Amines - chemical synthesis Catalysis copper enantioselective catalysis homopropargyl amines N-heterocyclic carbenes Pargyline - analogs & derivatives Pargyline - chemical synthesis propargyl additions Propylamines - chemical synthesis Stereoisomerism |
| Title | A Robust, Efficient, and Highly Enantioselective Method for Synthesis of Homopropargyl Amines |
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