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21st August 2013 @ 13:50

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Reaction information

*#Reaction file  
CSRxnsScheme_130f.cdx
*Reaction file type CDX
*Procedure  

General procedure D (see below) with diene 123c (100 mg, 0.27 mmol) and acrylonitrile (0.03 mL, 0.29 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave both the exo and endo isomers of the title compound:

The exo isomer (5-exo) was a colourless oil (16.2 mg, 13%). 

The endo isomer (5-endo) was a colourless oil (40.9 mg, 36%).

 

General procedure D:

The appropriate dienophile (1.1 eq.) was added to diene 123a,c or j (1 eq.) in benzene (1.00 mL). The reaction mixture was heated at reflux for 16 h. The solvent was removed in vacuo to give the crude product, which was purified as described.

*Yield (%)  13/36
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp100.pdf
AH Thesis_2011_pp176-223.pdf
Further information Compound 130f: exo-7-Butyl-1-tosyl-4-(trimethylsilyl)-2,3,4,5,6,7-hexahydro-1H-indole-5-carbonitrile

For multistep reactions (or their steps):

Overall reaction? True
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Attached Files
AH Thesis_2011_pp100.pdf
CSRxnsScheme_130f.cdx
AH Thesis_2011_pp176-223.pdf