title: 1,5-Asymmetric induction in boron-mediated aldol reactions of beta-alkoxy methylketones.
abstract: Good levels of substrate-controlled, 1,5- syn-stereoinduction are obtained in boron-mediated aldol reactions of beta-trichloromethyl-beta-alkoxy and beta-trifluoromethyl-beta-alkoxy methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group (TBS or PMB). In the case of boron aldol reactions of beta-aryl-beta-alkoxy methylketones, the 1,5- anti-adducts were obtained with high levels of diastereoselectivity only with a beta-OPMB group.
authors.affiliation: Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, 13084-971 Campinas, SP, Brazil. ldias@iqm.unicamp.br
authors.forename: Luiz C
authors.initials: LC
authors.lastname: Dias
authors.forename: Anderson A
authors.initials: AA
authors.lastname: de Marchi
authors.forename: Marco A B
authors.initials: MA
authors.lastname: Ferreira
authors.forename: Andrea M
authors.initials: AM
authors.lastname: Aguilar
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D001896:Boron Compounds; D007659:Ketones