7328-33-8Relevant articles and documents
Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition
Gandon, Vincent,Masson, Géraldine,Mati?i?, Mateja,Neuville, Luc,Van Elslande, Elsa,Varlet, Thomas
supporting information, p. 11611 - 11619 (2021/08/16)
A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.
Microwave-accelerated Ru-catalyzed hydrovinylation of alkynes and enynes: A straightforward approach toward 1,3-dienes and 1,3,5-trienes
Schabel, Tobias,Plietker, Bernd
, p. 6938 - 6941 (2013/06/27)
Quick, but not dirty! Microwave heating was found to have a significant effect on the Ru-catalyzed hydrovinylations of alkynes. A broad range of different terminal alkynes were coupled to methyl acrylate within just 30min in good to excellent yields (see scheme). This new protocol was transferred to the hydrovinylation of enynes as novel coupling partners in C-H-activation chemistry giving different 1,3,5-trienes as the sole products. Copyright
Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z,3Z)-butyltelluro-4-methoxy-1,3-butadiene
Dabdoub, Miguel J.,Dabdoub, Vania B.,Baroni, Adriano C.M.,Hurtado, Gabriela R.,Barbosa, Sandro L.
experimental part, p. 1666 - 1670 (2010/05/19)
(1Z,3Z)-Butyltelluro-4-methoxy-1,3-butadiene 2 was obtained by the hydrotelluration of (Z)-1-methoxy-but-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a-d with total retention of configuration. The alcohols formed undergo hydrolysis, resulting in the α,β,γ,δ-unsaturated aldehydes of (E,E) configuration, which are precursors of trienes obtained from natural sources. The products of this reaction were employed in the synthesis of methyl-(2E,4E)-decadienoate 7, which is a component of the flavor principles of ripe Bartlett pears. Performing the Wittig reaction of the methyl triphenylphosphorane with the deca-(2E,4E)-dienal 5a, we were able to synthesize the undeca-(1,3E,5E)-triene 6a. This compound is a sex-pheromone component of the marine brown algae Fucus serratus, Dictyopteris plagiograma, and Dictyopteris australis. Performing the Wittig reaction of methyl triphenylphosphorane with the octa-(2E,4E)-dienal 5c, the nona-(1,3E,5E)-triene 6b was synthesized. The compound obtained is a sex-pheromone component of the marine brown alga Sargassum horneri. The octa-(1,3E,5E)-triene 6c was easily obtained from hepta-(2E,4E)-dienal 5d by the Wittig reaction with methyl triphenylphophorane. This compound is a sex-pheromone component of the marine brown alga Fucus serratus.
