[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
[\/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=”||||||||”]Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92\u221298% ee\u2019s. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(\u2212)-3-n-butylphthalide is also presented.[\/et_pb_tab][et_pb_tab title=”PDF” _builder_version=”3.23.3″ link_option_url=”https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja907711a” 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\/ja907711a”]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=”2230″ 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
Phan, D. H. T.;\u00a0Kim, B.<\/u>; Dong, V. M. J. Am. Soc. Chem.\u00a02009<\/b>, 131, 15608\u201315609.<\/p>\n
[\/et_pb_text][\/et_pb_column][\/et_pb_row][\/et_pb_section]<\/p>\n","protected":false},"excerpt":{"rendered":"
2.\u00a0Phthalides by Rhodium-Catalyzed Ketone Hydroacylation Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92\u221298% […]<\/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-2225","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\/2225","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=2225"}],"version-history":[{"count":0,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts\/2225\/revisions"}],"wp:attachment":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/media?parent=2225"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/categories?post=2225"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/tags?post=2225"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}