Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N ‐Alkyl β‐Enamino Esters with Trichlorosilane and Water
2011; Wiley; Volume: 17; Issue: 10 Linguagem: Inglês
10.1002/chem.201003105
ISSN1521-3765
AutoresXinjun Wu, Yang Li, Chao Wang, Li Zhou, Xiaoxia Lü, Jian Sun,
Tópico(s)Chemical Synthesis and Analysis
ResumoChemistry – A European JournalVolume 17, Issue 10 p. 2846-2848 Communication Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N-Alkyl β-Enamino Esters with Trichlorosilane and Water Xinjun Wu, Xinjun Wu Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753 Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)Search for more papers by this authorYang Li, Yang Li Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorChao Wang, Chao Wang Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorLi Zhou, Li Zhou Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorProf. Dr. Xiaoxia Lu, Prof. Dr. Xiaoxia Lu Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorProf. Dr. Jian Sun, Corresponding Author Prof. Dr. Jian Sun sunjian@cib.ac.cn Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this author Xinjun Wu, Xinjun Wu Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753 Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)Search for more papers by this authorYang Li, Yang Li Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorChao Wang, Chao Wang Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorLi Zhou, Li Zhou Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorProf. Dr. Xiaoxia Lu, Prof. Dr. Xiaoxia Lu Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this authorProf. Dr. Jian Sun, Corresponding Author Prof. Dr. Jian Sun sunjian@cib.ac.cn Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China), Fax: (+86) 28-85222753Search for more papers by this author First published: 10 February 2011 https://doi.org/10.1002/chem.201003105Citations: 65Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl β-enamino esters 1 to give N-alkyl β-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme). Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_201003105_sm_miscellaneous_information.pdf7.7 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume17, Issue10March 1, 2011Pages 2846-2848 RelatedInformation
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