{"id":583,"date":"2007-08-08T09:53:35","date_gmt":"2007-08-08T14:53:35","guid":{"rendered":"http:\/\/scholarblogs.emory.edu\/davieslab\/?p=583"},"modified":"2018-07-12T14:01:49","modified_gmt":"2018-07-12T19:01:49","slug":"182-asymmetric-synthesis-of-tropanes-by-rhodium-catalyzed-4-3-cycloaddition","status":"publish","type":"post","link":"https:\/\/scholarblogs.emory.edu\/davieslab\/2007\/08\/08\/182-asymmetric-synthesis-of-tropanes-by-rhodium-catalyzed-4-3-cycloaddition\/","title":{"rendered":"182. Asymmetric Synthesis of Tropanes by Rhodium-Catalyzed [4 + 3] Cycloaddition"},"content":{"rendered":"<p>Authors:\u00a0Ravisekhara P. Reddy and Huw M. L. Davies<\/p>\n<p><em>J. Am. Chem. Soc., <\/em><\/p>\n<p><strong>2007<\/strong>, <em>129<\/em> (34), 10312\u201310313<\/p>\n<p><a href=\"http:\/\/scholarblogs.emory.edu\/davieslab\/files\/2013\/12\/014.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-medium wp-image-584 aligncenter\" alt=\"014\" src=\"http:\/\/scholarblogs.emory.edu\/davieslab\/files\/2013\/12\/014-300x84.gif\" width=\"300\" height=\"84\" \/><\/a><\/p>\n<p><!--more--><\/p>\n<p>Rhodium-catalyzed [4 + 3] cycloaddition between methyl 2-(siloxy)vinyldiazoacetate and pyrroles results in the enantioselective synthesis of highly functionalized 8-azabicyclo[3.2.1]octa-2,6-dienes (tropanes). The reaction proceeds via a rhodium\u2212carbenoid intermediate and involves a tandem cyclopropanation\/Cope rearrangement mechanism. The optimum chiral dirhodium catalyst for this transformation is the adamantyl <a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja072936e\" target=\"_blank\">glycine-derived complex, Rh2(S-PTAD)4.<\/a><\/p>\n<p><a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja072936e\" target=\"_blank\">Read More<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Authors:\u00a0Ravisekhara P. Reddy and Huw M. L. Davies J. Am. Chem. Soc., 2007, 129 (34), 10312\u201310313<\/p>\n","protected":false},"author":5441,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"ngg_post_thumbnail":0,"footnotes":""},"categories":[8],"tags":[12,59,90,14,37,76],"class_list":["post-583","post","type-post","status-publish","format-standard","hentry","category-publications","tag-heterocycles","tag-inter-molecular","tag-ptad","tag-rhodiumii","tag-tropane","tag-76"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.3 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>182. 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