ChemInform Abstract: Highly Diastereo- and Enantioselective Allylboration of Aldehydes Using α-Substituted Allyl/Crotyl Pinacol Boronic Esters via in situ Generated Borinic Esters

Autor: Jack L.-Y. Chen, Varinder K. Aggarwal, Christine L. Willis, Helen K. Scott, Matthew J. Hesse

Publikováno v: ChemInform. 44

Readily available, α-substituted allyl/crotyl pinacol boronic esters often give low E/Z selectivity (with Z favored) in reactions with aldehydes. We found that addition of nBuLi to the pinacol boronic ester followed by trapping of the alkoxide with

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::36187bbc630f5342a8045b0b0beae167
https://doi.org/10.1002/chin.201338057

Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters

Autor: Varinder K. Aggarwal, Christine L. Willis, Helen K. Scott, Jack L.-Y. Chen, Matthew J. Hesse

Publikováno v: Chen, J L-Y, Scott, H K, Hesse, M J, Willis, C L & Aggarwal, V K 2013, ' Highly Diastereo-and Enantioselective Allylboration of Aldehydes using alpha-Substituted Allyl/Crotyl Pinacol Boronic Esters via in Situ Generated Borinic Esters ', Journal of the American Chemical Society, vol. 135, no. 14, pp. 5316-5319 . https://doi.org/10.1021/ja401564z

Readily available, alpha-substituted allyl/crotyl pinacol boronic esters often give low E/Z selectivity (with Z favored) in reactions with aldehydes. We found that addition of nBuLi to the pinacol boronic ester followed by trapping of the alkoxide wi

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::26afc637456c082062a267187c4398df
https://pubmed.ncbi.nlm.nih.gov/23520993

Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres

Autor: Varinder K. Aggarwal, Helen K. Scott

Publikováno v: Chemistry (Weinheim an der Bergstrasse, Germany). 17(47)

Organoboron compounds are useful in asymmetric synthesis. We have developed an efficient methodology for the highly enantioselective synthesis of tertiary boronic esters from the corresponding secondary benzylic alcohols. Further stereospecific trans

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::dd719f63c925bf5cb1c9b584af60a372
https://pubmed.ncbi.nlm.nih.gov/22052475

Enantioselective construction of quaternary stereogenic centers from tertiary boronic esters: methodology and applications

Autor: Robin Larouche-Gauthier, Helen K. Scott, Varinder K. Aggarwal, Vishal Jheengut, Constantinos Rabalakos, Ravindra P. Sonawane

Publikováno v: Angewandte Chemie (International ed. in English). 50(16)

The creation of quaternary stereogenic centers with high enantioselectivity is challenging, in part, because of the high steric repulsion between the substituents on the carbon center that is generated during construction. Nevertheless, significant p

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4d70196ba32b1b5e5a0287be0bd627fe
https://pubmed.ncbi.nlm.nih.gov/21612008

Titelbild: Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications (Angew. Chem. 16/2011)

Autor: Vishal Jheengut, Constantinos Rabalakos, Helen K. Scott, Robin Larouche‐Gauthier, Ravindra P. Sonawane, Varinder K. Aggarwal

Publikováno v: Angewandte Chemie. 123:3655-3655

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::472dd4f7fba761b7fcb4d9b8c182da57
https://doi.org/10.1002/ange.201101504