Stairs, Shaun

Neves, Andre

Stöckmann, Henning

Wainman, Yelena A

Ireland-Zecchini, Heather

Brindle, Kevin

Leeper, Finian

Journal of the American Chemical Society

Enantioenriched secondary allylic carbamates have been deprotonated with sBuLi and reacted with boronic esters. In contrast to other electrophiles, high alpha-selectivity was observed and the boronate complexes were formed with almost complete retention of stereochemistry. The boronate complexes underwent a stereospecific 1,2-migration leading to tertiary allylic boronic esters with high er (&gt;98:2). The scope of the reaction has been explored and found to embrace a broad range of both allylic carbamates and boronic esters. The methodology has been applied to an eight-step, stereoselective synthesis of each of the diastereoisomers of C30 botryococcene.</p

Pulis, Alexander P.

Aggarwal, Varinder K.

Explore Bristol Research

Synthesis of Enantioenriched Tertiary Boronic Esters from Secondary Allylic Carbamates. Application to the Synthesis of C30 Botryococcene

Pulis, A. P.

Aggarwal, V. K.

The University of Manchester - Institutional Repository

Seeing the sugar coating: N-Acetyl-glucosamine and mannosamine derivatives tagged with an isonitrile group are metabolically incorporated into cell-surface glycans and can be detected with a fluorescent tetrazine. This bioorthogonal isonitrile-tetrazine ligation is also orthogonal to the commonly used azide-cyclooctyne ligation, and so will allow simultaneous detection of the incorporation of two different sugars

Neves, André A

Brindle, Kevin M

Leeper, Finian J

Apollo (Cambridge)