Stereocontrolled Synthesis of 1, 5-Stereogenic Centers through Three-Carbon Homologation of Boronic Esters

Unsworth, P. J., Leonori, D., & Aggarwal, V. K.

Angewandte Chemie International Edition 53.37 (2014): 9846-9850.

Allylic pinacol boronic esters are stable toward 1,3-borotropic rearrangement. We developed a PdII-mediated isomerization process that gives di- or trisubstituted allylic boronic esters with high E selectivity. The combination of this method with lithiation–borylation enables the synthesis of carbon chains that bear 1,5-stereogenic centers. The utility of this method has been demonstrated in a formal synthesis of (+)‐jasplakinolide.


Products Used in this Publication

Catalog NumberCASProduct NamePrice

Related Products

Catalog NumberCASProduct NamePrice
B0001-054910113-73-5Gramicidin SInquiry
B0001-1498097161-73-1Thiocholine iodideInquiry
B0001-186805203787-91-1Salcaprozate sodium, 99%Inquiry
B0001-3946391341-23-7Nicotinamide Riboside (Contain ~80% food grade dextrin as stabilizer)Inquiry
Price Inquiry