{"id":2222,"date":"2020-04-20T03:06:35","date_gmt":"2020-04-20T03:06:35","guid":{"rendered":"https:\/\/scienceweb.clemson.edu\/boni\/?p=2222"},"modified":"2020-05-21T22:52:19","modified_gmt":"2020-05-21T22:52:19","slug":"distal-stereocontrol-using-guanidinylated-peptides-as-multifunctional-ligands-desymmetrization-of-diarylmethanes-via-ullmann-cross-coupling","status":"publish","type":"post","link":"https:\/\/scienceweb.clemson.edu\/kimgroup\/distal-stereocontrol-using-guanidinylated-peptides-as-multifunctional-ligands-desymmetrization-of-diarylmethanes-via-ullmann-cross-coupling\/","title":{"rendered":"Distal Stereocontrol Using\u00a0Guanidinylated\u00a0Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullmann Cross-Coupling"},"content":{"rendered":"

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4.<\/strong><\/span>\u00a0Distal Stereocontrol Using\u00a0Guanidinylated\u00a0Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullmann Cross-Coupling<\/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 the development of a new class of guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates. Our mechanistic studies suggest that distal stereocontrol is achieved through a Cs-bridged interaction between the Lewis-basic C-terminal carboxylate of the peptides with the distal arene of the substrate.[\/et_pb_tab][et_pb_tab title=”PDF” _builder_version=”3.23.3″ link_option_url=”https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6b03444″ 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:\/\/pubs.acs.org\/doi\/10.1021\/jacs.6b03444″]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=”2224″ 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

Kim, B.<\/u>; Chinn, A. J.; Fandrick, D. R.; Senanayake, C. H.; Singer, R. A.; Miller, S. J. J. Am. Chem. Soc.\u00a02016<\/b>, 138, 7939\u20137945.<\/p>\n

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4.\u00a0Distal Stereocontrol Using\u00a0Guanidinylated\u00a0Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullmann Cross-Coupling We report the development of a new class of guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields […]<\/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-2222","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\/2222","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=2222"}],"version-history":[{"count":0,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts\/2222\/revisions"}],"wp:attachment":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/media?parent=2222"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/categories?post=2222"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/tags?post=2222"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}