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Synthesis 2014; 46(24): 3383-3393
DOI: 10.1055/s-0034-1379072
DOI: 10.1055/s-0034-1379072
paper
Enantioselective N-Allylic Alkylation of N-Propargylsulfonamides with Morita–Baylis–Hillman Carbonates and Sequential Electrophilic Cyclization
Further Information
Publication History
Received: 17 June 2014
Accepted after revision: 11 August 2014
Publication Date:
04 September 2014 (online)
Abstract
The enantioselective N-allylic alkylation of N-propargylsulfonamides with racemic Morita–Baylis–Hillman (MBH) carbonates catalyzed by modified cinchona alkaloids has been investigated. The alkylation products from MBH carbonates with a 4-methoxyphenyl group underwent ipso-iodocyclization to give optically active azaspirocyclohexadienones via electrophilic activation of alkyne group with iodine monochloride. In contrast, ortho-selective intramolecular Friedel–Crafts reaction occurred for intermediates from MBH carbonates with other electron-rich or neutral aryl or heteroaryl substitutions via the same activation strategy, delivering multifunctional 2-benzazepine frameworks in a highly enantioenriched form.
Key words
Morita–Baylis–Hillman carbonates - asymmetric allylic alkylation - electrophilic cyclization - azaspirocyclohexadienones - 2-benzazepinesSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
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For selected examples:
For a review, see:
For selected examples:
For a review, see:
For iso-selective examples, see:
For ortho-selective examples, see: