A Brønsted Acid-Primary Amine as a Synergistic Catalyst for Stereoselective Asymmetric Diels-Alder Reactions

Herein, we present the Brønsted‐acid‐controlled, primary‐amine‐catalyzed stereoselective asymmetric synthesis of druglike six‐membered spirooxindoles from simple aliphatic substrates through a Barbas [4+2]‐cycloaddition reaction by using 2‐aminobuta‐1,3‐diene catalysis under ambient conditions. An e...

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Bibliographic Details
Published in:	European journal of organic chemistry Vol. 2016; no. 31; pp. 5220 - 5226
Main Authors:	Ramachary, Dhevalapally B., Reddy, P. Sreekanth, Shruthi, Kodambahalli S., Madhavachary, R., Reddy, P. V. Govardhana
Format:	Journal Article
Language:	English
Published:	Weinheim Blackwell Publishing Ltd 01-11-2016 Wiley Subscription Services, Inc
Subjects:	Cycloaddition Dienes Ketones Organocatalysis Spiro compounds
Online Access:	Get full text
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Summary:	Herein, we present the Brønsted‐acid‐controlled, primary‐amine‐catalyzed stereoselective asymmetric synthesis of druglike six‐membered spirooxindoles from simple aliphatic substrates through a Barbas [4+2]‐cycloaddition reaction by using 2‐aminobuta‐1,3‐diene catalysis under ambient conditions. An effective Barbas [4+2]‐cycloaddition is disclosed to access druglike six‐membered spirooxindoles from simple aliphatic substrates in good yields with excellent enantioselectivities through synergistic amine/acid catalysis. DCE = 1,2‐dichloroethane.
Bibliography:	ArticleID:EJOC201601011 istex:44DFAA94D6C069D77BC9B1E44E553AB4BBC7B5BC Science and Engineering Research Board - Grant No. EMR/2015/000860 Supporting Information ark:/67375/WNG-D0S2BKCM-M
ISSN:	1434-193X 1099-0690
DOI:	10.1002/ejoc.201601011