beta-hydroxy esters using\u00a0superbase<\/a>s such as\u00a0LDA<\/a>\u00a0or\u00a0LiHMDS<\/a>.<\/p>\n

This\u00a0organic reaction<\/a>\u00a0was first reported by G. Fr\u00e1ter in 1979 (DOI<\/a>\u00a0DOI<\/a>).
\n
\nIn the original Fr\u00e1ter publication the starting material is\u00a0ethyl acetoacetate<\/a>\u00a01, stereoselectively converted to the beta-hydroxy ester 2 with\u00a0Baker’s yeast<\/a>, converted to the dianion 3 with LDA and finally alkylated with\u00a0iodomethane<\/a>in\u00a0HMPA<\/a>\u00a0to 4.<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

<\/center><\/center><\/center><\/center><\/center><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n","protected":false},"excerpt":{"rendered":"

The Fr\u00e1ter-Seebach alkylation is the\u00a0stereoselective\u00a0alkylation\u00a0of\u00a0chiral beta-hydroxy esters using\u00a0superbases such as\u00a0LDA\u00a0or\u00a0LiHMDS. This\u00a0organic reaction\u00a0was first reported by G. Fr\u00e1ter in 1979 (DOI\u00a0DOI). In the original Fr\u00e1ter publication the starting material is\u00a0ethyl acetoacetate\u00a01, stereoselectively converted to the beta-hydroxy ester 2 with\u00a0Baker’s yeast, converted to the dianion 3 with LDA and finally alkylated with\u00a0iodomethanein\u00a0HMPA\u00a0to 4.<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[143],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/43"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=43"}],"version-history":[{"count":1,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/43\/revisions"}],"predecessor-version":[{"id":44,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/43\/revisions\/44"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=43"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=43"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=43"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}