{"id":2208,"date":"2020-04-20T02:44:51","date_gmt":"2020-04-20T02:44:51","guid":{"rendered":"https:\/\/scienceweb.clemson.edu\/boni\/?p=2208"},"modified":"2020-05-21T22:52:18","modified_gmt":"2020-05-21T22:52:18","slug":"enantioselective-intermolecular-c-o-bond-formation-in-the-desymmetrization-of-diarylmethines-employing-a-guanidinylated-peptide-based-catalyst","status":"publish","type":"post","link":"https:\/\/scienceweb.clemson.edu\/kimgroup\/enantioselective-intermolecular-c-o-bond-formation-in-the-desymmetrization-of-diarylmethines-employing-a-guanidinylated-peptide-based-catalyst\/","title":{"rendered":"Enantioselective Intermolecular C-O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst"},"content":{"rendered":"

[et_pb_section fb_built=”1″ admin_label=”Class Details Section” _builder_version=”3.23.3″ background_color=”#ffffff” custom_padding=”0px||0px|”][et_pb_row custom_padding=”||5px|||” _builder_version=”3.23.3″][et_pb_column type=”4_4″ _builder_version=”3.23.3″][et_pb_text _builder_version=”3.23.3″ custom_margin=”||15px|||”]<\/p>\n

6.<\/strong><\/span>\u00a0Enantioselective Intermolecular C-O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst <\/b><\/h1>\n

[\/et_pb_text][\/et_pb_column][\/et_pb_row][et_pb_row _builder_version=”3.23.3″][et_pb_column type=”4_4″ _builder_version=”3.23.3″][et_pb_tabs active_tab_background_color=”#109dc0″ inactive_tab_background_color=”#109dc0″ active_tab_text_color=”#ffffff” _builder_version=”3.23.3″ tab_text_color=”#ffffff” body_font=”||||||||” tab_font=”||||||||” tab_line_height=”1.8em”][et_pb_tab title=”\u00bb” _builder_version=”3.23.3″][\/et_pb_tab][et_pb_tab title=”ABSTRACT” _builder_version=”3.23.3″ body_font=”||||||||” tab_font=”||||||||”]We report a series of enantioselective C-O bond cross-coupling reactions based on remote symmetry breaking processes in diarylmethine substrates. The key to the chemistry is multifunctional guanidinylated peptide-based ligands that allow highly selective, intermolecular Cu-catalyzed cross-coupling of phenolic nucleophiles. The scope of the process is explored, demonstrating efficiency for substrates with a range of electronic and steric perturbations to the nucleophile. Scope and limitations are also reported for variation of the diarylmethine. While the presence of an intervening tBu group is found to be optimal for maximum enantioselectivity, several other substituents may also be present such that appreciable selectivity can be achieved, providing an uncommon level of scope for diarylmethine desymmetrizations. In addition, chemoselective reactions are possible when there are phenolic hydroxyl groups within substrates that contain a second reactive site, setting the stage for applications in diverse complex molecular settings. [\/et_pb_tab][et_pb_tab title=”PDF” _builder_version=”3.23.3″ link_option_url=”https:\/\/www.ncbi.nlm.nih.gov\/pmc\/articles\/PMC5738244\/pdf\/nihms926561.pdf” link_option_url_new_window=”on”]Download PDF »[\/et_pb_tab][et_pb_tab title=”SUPPORTING INFORMATION” _builder_version=”3.23.3″ link_option_url=”https:\/\/www.ncbi.nlm.nih.gov\/pmc\/articles\/PMC5738244\/”]View on PubMed »[\/et_pb_tab][\/et_pb_tabs][\/et_pb_column][\/et_pb_row][et_pb_row _builder_version=”3.23.3″][et_pb_column type=”4_4″ _builder_version=”3.23.3″][et_pb_gallery gallery_ids=”2210,2211,2212″ fullwidth=”on” _builder_version=”3.23.3″][\/et_pb_gallery][\/et_pb_column][\/et_pb_row][et_pb_row _builder_version=”3.23.3″][et_pb_column type=”4_4″ _builder_version=”3.23.3″][et_pb_text _builder_version=”3.23.3″]<\/p>\n

Chinn, A. J.;\u00a0Kim, B.<\/u>; Kwon. Y.; Miller, S. J. J. Am. Chem. Soc.\u00a02017<\/b>, 139, 18107\u201318114.<\/p>\n

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6.\u00a0Enantioselective Intermolecular C-O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst We report a series of enantioselective C-O bond cross-coupling reactions based on remote symmetry breaking processes in diarylmethine substrates. The key to the chemistry is multifunctional guanidinylated peptide-based ligands that allow highly selective, intermolecular Cu-catalyzed cross-coupling of phenolic nucleophiles. The […]<\/p>\n","protected":false},"author":4,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"on","_et_pb_old_content":"","_et_gb_content_width":"","footnotes":""},"categories":[11,13],"tags":[],"class_list":["post-2208","post","type-post","status-publish","format-standard","hentry","category-catalysis","category-prior-to-clemson"],"_links":{"self":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts\/2208","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/comments?post=2208"}],"version-history":[{"count":0,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts\/2208\/revisions"}],"wp:attachment":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/media?parent=2208"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/categories?post=2208"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/tags?post=2208"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}