Stereoselective synthesis of highly substituted cyclohexanes by a rhodium-carbene initiated domino sequence.

Brendan T Parr, Huw M L Davies

Organic letters 2015 Feb 20

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A stereoselective synthesis of cyclohexanes bearing four stereocenters from vinyldiazoacetates and allyl alcohols by a rhodium-carbene initiated domino reaction is described. The reaction cascade features a tandem ylide formation/[2,3]-sigmatropic rearrangement, oxy-Cope rearrangement, and type II carbonyl ene reaction, all of which proceed with a high degree of stereocontrol. The products are routinely isolated with excellent stereocontrol (>97:3 dr, 99% ee).

Citation

Brendan T Parr, Huw M L Davies. Stereoselective synthesis of highly substituted cyclohexanes by a rhodium-carbene initiated domino sequence. Organic letters. 2015 Feb 20;17(4):794-7