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Synfacts 2017; 13(10): 1073
DOI: 10.1055/s-0036-1591278
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Boron Alkylidene–Alkene Cycloaddition

Contributor(s):
Paul Knochel
,
Ferdinand H. Lutter
Liu X. Deaton TM. Haeffner F. Morken JP. * Boston College, Chestnut Hill, USA
A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Angew. Chem. Int. Ed. 2017;
56: 11485-11489
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Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Key words

boron - cycloaddition - diastereoselective synthesis

Significance

An intramolecular [2+2] cycloaddition of geminal bis(boronates) with unactivated alkenes using t-BuOK is reported. An intermediate bicyclic ‘ate’ complex is quenched with various electrophiles to obtain polysubstituted cyclopentanes in high diastereoselectivity.


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Comment

The method was successfully applied for the synthesis of the natural bicyclic terpene aphanamal. The key [2+2] cycloaddition step proceeds in 65% yield and with good stereoselectivity.


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