TMSOTf-mediated synthesis of skipped dienes through the addition of olefins to imines and semicyclic ,-acetals

A novel approach to skipped dienes has been developed through the TMSOTf-mediated one-pot addition-substitution of olefins 2a , 2f and 2g with imines 1a-1g , and a series of aryl substituted skipped dienes 3aa-3gf were accordingly obtained in 62%-94% yields. Moreover, semicyclic N , O -acetals 5 and...

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Published in:Organic & biomolecular chemistry 2021-09, Vol.19 (36), p.7883-7893
Main Authors: Feng, Yi-Man, Nie, Xiao-Di, Sun, Jian-Ting, Xu, Wen-Ke, Wei, Bang-Guo
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Summary:A novel approach to skipped dienes has been developed through the TMSOTf-mediated one-pot addition-substitution of olefins 2a , 2f and 2g with imines 1a-1g , and a series of aryl substituted skipped dienes 3aa-3gf were accordingly obtained in 62%-94% yields. Moreover, semicyclic N , O -acetals 5 and 7 could also undergo this transformation to produce the corresponding skipped dienes 6aa and 6af-6al and 8ba and 8bf-8bk in moderate to good yields. A novel approach to skipped dienes has been developed through the TMSOTf-mediated addition-substitution of olefins 2a , 2f and 2g with imines 1a-1g , and a series of aryl substituted skipped dienes 3aa-3gf were accordingly obtained in 62%-94% yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01370j