{"id":649,"date":"2010-02-19T12:37:09","date_gmt":"2010-02-19T17:37:09","guid":{"rendered":"http:\/\/scholarblogs.emory.edu\/davieslab\/?p=649"},"modified":"2018-07-12T14:01:43","modified_gmt":"2018-07-12T19:01:43","slug":"206-controlling-factors-for-c%e2%88%92h-functionalization-versus-cyclopropanation-of-dihydronaphthalenes","status":"publish","type":"post","link":"https:\/\/scholarblogs.emory.edu\/davieslab\/2010\/02\/19\/206-controlling-factors-for-c%e2%88%92h-functionalization-versus-cyclopropanation-of-dihydronaphthalenes\/","title":{"rendered":"206. Controlling Factors for C\u2212H Functionalization versus Cyclopropanation of Dihydronaphthalenes"},"content":{"rendered":"<p>Authors:\u00a0Etienne Nadeau, Dominic L. Ventura, Jonathan A. Brekan and Huw M. L. Davies<\/p>\n<p><em>J. Org. Chem., <\/em><\/p>\n<p><strong>2010<\/strong>, <em>75<\/em> (6), 1927\u20131939<\/p>\n<p><a href=\"http:\/\/scholarblogs.emory.edu\/davieslab\/files\/2013\/12\/023.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-medium wp-image-650 aligncenter\" alt=\"023\" src=\"http:\/\/scholarblogs.emory.edu\/davieslab\/files\/2013\/12\/023-300x64.gif\" width=\"300\" height=\"64\" \/><\/a><\/p>\n<p><!--more--><\/p>\n<p>Rhodium(II)-catalyzed reactions of vinyldiazoacetates with dihydronaphthalenes were systematically studied. These substrates underwent cyclopropanantion and\/or the combined C\u2212H activation\/Cope rearrangement in good overall yield and with good diastereo- and enantiocontrol. The selectivity of these reactions was profoundly influenced by the nature of the chiral catalyst, the vinyldiazoacetate, and the dihydronaphthalene. The best combinations for achieving the highest selectivity in the cyclopropanation and the combined C\u2212H activation\/Cope rearrangement of 1,2-dihydronaphthalenes are methyl 2-diazopent-3-enoate (2a)\/Rh2(S-DOSP)4 and methyl 3-(tert-butyldimethylsilyloxy)-2-diazopent-3-enoate (2b)\/Rh2(S-PTAD)4. These combinations are very effective at enantiodivergent reactions of 1-methyl-1,2-dihydronaphthalenes.<\/p>\n<p><a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo902644f?prevSearch=%255Bauthor%253A%2BHuw%2BM.%2BL.%2BDavies%255D%2BNOT%2B%255Batype%253A%2Bad%255D%2BNOT%2B%255Batype%253A%2Bacs-toc%255D&amp;searchHistoryKey=\" target=\"_blank\">Read More<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Authors:\u00a0Etienne Nadeau, Dominic L. Ventura, Jonathan A. Brekan and Huw M. L. Davies J. Org. Chem., 2010, 75 (6), 1927\u20131939<\/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":[16,7,90,14,30],"class_list":["post-649","post","type-post","status-publish","format-standard","hentry","category-publications","tag-carbenoid","tag-dosp","tag-ptad","tag-rhodiumii","tag-vinyl-carbenoid"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.3 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>206. 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