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. 2012 Jul 2;51(27):6613-7.
doi: 10.1002/anie.201202856. Epub 2012 May 25.

Copper-catalyzed enantioselective allylic substitution with readily accessible carbonyl- and acetal-containing vinylboron reagents

Fang Gao  1 , James L Carr, Amir H Hoveyda
Affiliations

Copper-catalyzed enantioselective allylic substitution with readily accessible carbonyl- and acetal-containing vinylboron reagents

Fang Gao et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Scheme 1
Scheme 1
A route for enantioselective synthesis of Pummerer ketone might involve catalytic allylic substitution with a carbonyl-containing vinyl group followed by a catalytic diastereoselective intramolecular conjugate addition and catalytic ring-closing metathesis. pg = protecting group.
Scheme 2
Scheme 2
Products of NHC–Cu-catalyzed EAS of various trisubstituted allylic phosphates and different readily accessible vinylborons. All reactions were performed with 5.5 mol % 6b; see Table 2 for conditions and the Supporting Information for details).
Scheme 3
Scheme 3
NHC–Cu-catalyzed EAS with allylic phosphates and carboxylic ester containing vinylboron 13.
Scheme 4
Scheme 4
NHC–Cu-catalyzed EAS of allylic phosphates with acetal-containing alkenylboron 16.
Scheme 5
Scheme 5
Syntheses of Pummerer ketone and its anti isomer involving NHC–Cu-catalyzed EAS, cinchona alkaloid-catalyzed diastereoselective intramolecular conjugate addition and Ru-catalyzed ring-closing metathesis.
See this image and copyright information in PMC

References

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