logo
CONTENT TYPES

Efficient Synthesis of α-Tertiary α-Silylamines from Aryl Sulfonylimidates via One-Pot, Sequential C–Si/C–C Bond Formations

View Author Information
Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences, Urumqi 830011, China and Graduate University of the Chinese Academy of Sciences
Cite this: Org. Lett. 2012, 14, 11, 2906–2909
Publication Date (Web):May 23, 2012
https://doi.org/10.1021/ol301194e
Copyright © 2012 American Chemical Society
Article Views
1914
Altmetric
-
Citations
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Read OnlinePDF (212 KB)
Supporting Info (1)»

Abstract

Abstract Image

An efficient and flexible route for the synthesis of α-tertiary (α,α-dibranched) α-silylamines via sequential reactions of sulfonylimidates using readily available phenyldimethylsilyllithium and Grignard reagents is described. The procedure allows successive formation of C–Si/C–C bonds in a single flask.

Supporting Information

ARTICLE SECTIONS
Jump To

Experimental details and characterization data. This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 19 publications.

  1. Sylvain Henrion, Bertrand Carboni, Fernando P. Cossío, Thierry Roisnel, Jose M. Villalgordo, and François Carreaux . Stereospecific Synthesis of α-Amino Allylsilane Derivatives through a [3,3]-Allyl Cyanate Rearrangement. Mild Formation of Functionalized Disiloxanes. The Journal of Organic Chemistry 2016, 81 (11) , 4633-4644. https://doi.org/10.1021/acs.joc.6b00505
  2. Chao-Yang Lin, Zhao Sun, Yan-Jun Xu, and Chong-Dao Lu . Synthesis of Aryl anti-Vicinal Diamines via Aza-Brook Rearrangement-Initiated Nucleophilic Addition of α-Silylamines to Imines. The Journal of Organic Chemistry 2015, 80 (7) , 3714-3722. https://doi.org/10.1021/acs.joc.5b00255
  3. Yasuhiro Kondo, Michiko Sasaki, Masatoshi Kawahata, Kentaro Yamaguchi, and Kei Takeda . Enantioselective Synthesis of α-Silylamines by Meerwein–Ponndorf–Verley-Type Reduction of α-Silylimines by a Chiral Lithium Amide. The Journal of Organic Chemistry 2014, 79 (8) , 3601-3609. https://doi.org/10.1021/jo500441a
  4. Jiu-Long Jiang, Ming Yao, and Chong-Dao Lu . Efficient Synthesis of α-Quaternary α-Hydroxy-β-amino Esters via Silyl Glyoxylate-Mediated Three-Component Reactions. Organic Letters 2014, 16 (1) , 318-321. https://doi.org/10.1021/ol403388w
  5. Xiao-Chuan Cai and Barry B. Snider . Synthesis of the Spiroiminal Moiety and Approaches to the Synthesis of Marineosins A and B. The Journal of Organic Chemistry 2013, 78 (23) , 12161-12175. https://doi.org/10.1021/jo402178r
  6. Geanna K. Min, Dácil Hernández, and Troels Skrydstrup . Efficient Routes to Carbon–Silicon Bond Formation for the Synthesis of Silicon-Containing Peptides and Azasilaheterocycles. Accounts of Chemical Research 2013, 46 (2) , 457-470. https://doi.org/10.1021/ar300200h
  7. Juliet M. Alderson, Jennifer M. Schomaker. Tandem Oxidative Derivatization of Nitrene Insertion Products for the Highly Diastereoselective Synthesis of 1,3-aminoalcohols. Chemistry - A European Journal 2017, 23 (36) , 8571-8576. https://doi.org/10.1002/chem.201702038
  8. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Janice Smith. Grignard reagents. 2017,,https://doi.org/10.1002/9780471264194.fos05425.pub5
  9. Jiawei Rong, Juan F. Collados, Pablo Ortiz, Ravindra P. Jumde, Edwin Otten, Syuzanna R. Harutyunyan. Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines. Nature Communications 2016, 7 (1) https://doi.org/10.1038/ncomms13780
  10. Koki Hotoda, Asami Ohnuma, Kosuke Kusakabe, Aki Tanaka, Ikuo Sasaki, Hideyuki Sugimura. Stereoselective synthesis of the (−)-dysiherbaine furopyran core via BF3-promoted formal [3+2] annulation of aldehydo-aldoses with allylsilanes. Tetrahedron Letters 2016, 57 (48) , 5359-5362. https://doi.org/10.1016/j.tetlet.2016.10.073
  11. Tao Guo, Ying-Chao Liu, Bo Li, Hong-Min Liu. Convenient synthesis of α,α-(bisallyl and bispropargyl)-substituted amines via aza-Barbier-type reaction. Tetrahedron Letters 2015, 56 (19) , 2469-2471. https://doi.org/10.1016/j.tetlet.2015.03.103
  12. Yutaro Yamamoto, Hiroshi Matsubara, Kei Murakami, Hideki Yorimitsu, Atsuhiro Osuka. Activator-Free Palladium-Catalyzed Silylation of Aryl Chlorides with Silylsilatranes. Chemistry - An Asian Journal 2015, 10 (1) , 219-224. https://doi.org/10.1002/asia.201402595
  13. Wook Jeong, Jungjoon Kim, Jaiwook Park, Young Ho Rhee. Stereoselective Synthesis of Highly Substituted α-Silylamines from Silylmethyl Azides under Ru Catalysis. European Journal of Organic Chemistry 2014, 2014 (34) , 7577-7581. https://doi.org/10.1002/ejoc.201403200
  14. Chunliang Zhao, Chenran Jiang, Jing Wang, Cai Wu, Qing-Wei Zhang, Wei He. Enantioselective Syntheses of α-Silyl Amines via a Copper-N-Heterocyclic Carbene Catalyzed Nucleophilic Silicon Transfer to Imines. Asian Journal of Organic Chemistry 2014, 3 (8) , 851-855. https://doi.org/10.1002/ajoc.201402077
  15. Alexander Hensel, Kazuhiko Nagura, Lukas B. Delvos, Martin Oestreich. Enantioselektive Addition von Siliciumnukleophilen an Aldimine mit einem präformierten NHC-Kupfer(I)-Komplex als Katalysator. Angewandte Chemie 2014, 126 (19) , 5064-5067. https://doi.org/10.1002/ange.201402086
  16. Alexander Hensel, Kazuhiko Nagura, Lukas B. Delvos, Martin Oestreich. Enantioselective Addition of Silicon Nucleophiles to Aldimines Using a Preformed NHC-Copper(I) Complex as the Catalyst. Angewandte Chemie International Edition 2014, 53 (19) , 4964-4967. https://doi.org/10.1002/anie.201402086
  17. Kai-Jiong Xiao, Jie-Min Luo, Xiao-Er Xia, Yu Wang, Pei-Qiang Huang. General One-Pot Reductive gem -Bis-Alkylation of Tertiary Lactams/Amides: Rapid Construction of 1-Azaspirocycles and Formal Total Synthesis of (±)-Cephalotaxine. Chemistry - A European Journal 2013, 19 (39) , 13075-13086. https://doi.org/10.1002/chem.201302096
  18. Yuta Yanagita, Hugh Nakamura, Kenji Shirokane, Yusuke Kurosaki, Takaaki Sato, Noritaka Chida. Direct Nucleophilic Addition to N- Alkoxyamides. Chemistry - A European Journal 2013, 19 (2) , 678-684. https://doi.org/10.1002/chem.201202639
  19. Xiao-Jun Han, Ming Yao, Chong-Dao Lu. ChemInform Abstract: Efficient Synthesis of α-Tertiary α-Silylamines from Aryl Sulfonylimidates via One-Pot, Sequential C-Si/C-C Bond Formations.. ChemInform 2012, 43 (40) , no-no. https://doi.org/10.1002/chin.201240200

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE