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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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 51; no. 27; pp. 6618 - 6621
Main Authors:	Vieira, Erika M., Haeffner, Fredrik, Snapper, Marc L., Hoveyda, Amir H.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 02-07-2012 WILEY‐VCH Verlag
Subjects:	Amines - chemical synthesis Catalysis copper enantioselective catalysis homopropargyl amines N-heterocyclic carbenes Pargyline - analogs & derivatives Pargyline - chemical synthesis propargyl additions Propylamines - chemical synthesis Stereoisomerism
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Summary:	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.
Bibliography:	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
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201202694