120467-64-3Relevant academic research and scientific papers
Organic chemistry: Functionalization of C(sp3)-H bonds using a transient directing group
Zhang, Fang-Lin,Hong, Kai,Li, Tuan-Jie,Park, Hojoon,Yu, Jin-Quan
, p. 252 - 256 (2016)
Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity in carbon-hydrogen (C-H) bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and, often, applicability as well. Here we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C-H bonds. Arylation of a wide range of aldehydes and ketones at the β or γ positions proceeds in the presence of a palladium catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C-H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.
SYNTHESIS OF JUVABIONE ANALOGUES
Mane, Ramchandra B.,Desai, Uday V.,Hebbalkar, Geeta D.
, p. 646 - 657 (2007/10/02)
Alkylation of various β-ketoesters IIIa-d with bis(p-methoxycarbonylphenyl)bromomethane (II) and bis(p-chlorophenyl)bromomethane (VI) followed by cleavage of ethoxycarbonyl group or hydrolysis and esterification gave methoxycarbonylphenyl and chlorophenyl analogues of ar-juvabione, respectively.Condensation of bis(p-methoxycarbonylphenyl)methanol (IX) with isovaleryl and trichloroacetyl chloride gave isovalerate X and trichloroacetate XI, respectively, while the condensation of bis(p-chlorophenyl)methanol (XII) with isovaleryl chloride and citronellyl bromide yieldedisovalerate XIII and citronellyl ether XIV, respectively.The methoxycarbonylation of aryl-alkyl ketones XVa-d with oxalyl chloride and treatment with methanol furnished various ar-juvabione analogues XVIa-d.The compounds Vb, Vc, Vd, XVIb, and XVIc showed high activity against Dysdercus koenigii at 1μg concentration.
