{"id":2177,"date":"2020-04-20T02:11:29","date_gmt":"2020-04-20T02:11:29","guid":{"rendered":"https:\/\/scienceweb.clemson.edu\/boni\/?p=2177"},"modified":"2020-05-21T22:52:18","modified_gmt":"2020-05-21T22:52:18","slug":"divergent-control-of-point-and-axial-stereogenicity-catalytic-enantioselective-c-n-bond-forming-cross-coupling-and-catalyst-controlled-atroposelective-cyclodehydration","status":"publish","type":"post","link":"https:\/\/scienceweb.clemson.edu\/kimgroup\/divergent-control-of-point-and-axial-stereogenicity-catalytic-enantioselective-c-n-bond-forming-cross-coupling-and-catalyst-controlled-atroposelective-cyclodehydration\/","title":{"rendered":"Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C-N Bond-Forming Cross-Coupling and Catalyst-Controlled Atroposelective Cyclodehydration"},"content":{"rendered":"

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7.<\/strong><\/span>\u00a0Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C-N Bond-Forming Cross-Coupling and Catalyst-Controlled Atroposelective Cyclodehydration <\/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=”||||||||”]Catalyst control over reactions that produce multiple stereoisomers is a challenge in synthesis. Control over reactions that involve stereogenic elements remote from one another is particularly uncommon. Additionally, catalytic reactions that address both stereogenic carbon centers and an element of axial chirality are also rare. Reported herein is a catalytic approach to each stereoisomer of a scaffold containing a stereogenic center remote from an axis of chirality. Newly developed peptidyl copper complexes catalyze an unprecedented remote desymmetrization involving enantioselective C-N bond-forming cross-coupling. Then, chiral phosphoric acid catalysts set an axis of chirality through an unprecedented atroposelective cyclodehydration to form a heterocycle with high diastereoselectivity. The application of chiral copper complexes and phosphoric acids provides access to each stereoisomer of a framework with two different elements of stereogenicity. [\/et_pb_tab][et_pb_tab title=”PDF” _builder_version=”3.23.3″ link_option_url=”https:\/\/www.ncbi.nlm.nih.gov\/pmc\/articles\/PMC5964046\/pdf\/nihms965698.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\/PMC5964046\/”]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=”2197,2198,2199,2200″ 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

Kwon, Y.; Chinn, A. J.;\u00a0Kim, B.<\/u>; Miller, S. J. Angew. Chem. Int. Ed.\u00a02018<\/b>, 57, 6251\u20136255.<\/p>\n

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7.\u00a0Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C-N Bond-Forming Cross-Coupling and Catalyst-Controlled Atroposelective Cyclodehydration Catalyst control over reactions that produce multiple stereoisomers is a challenge in synthesis. Control over reactions that involve stereogenic elements remote from one another is particularly uncommon. Additionally, catalytic reactions that address both stereogenic carbon centers and an element […]<\/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-2177","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\/2177","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=2177"}],"version-history":[{"count":0,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts\/2177\/revisions"}],"wp:attachment":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/media?parent=2177"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/categories?post=2177"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/tags?post=2177"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}