1072925-56-4Relevant articles and documents
Intermolecular enantioselective Heck-Matsuda arylations of acyclic olefins: Application to the synthesis of β-aryl-γ-lactones and β-aryl aldehydes
Oliveira, Caio C.,Angnes, Ricardo A.,Correia, Carlos Roque D.
, p. 4373 - 4385 (2013/06/27)
We describe herein a synthetically useful method for the enantioselective intermolecular Heck-Matsuda arylation of acyclic allylic alcohols. Aryldiazonium tetrafluoroborates were applied as arylating agents in the presence of Pd(TFA)2 and a chiral, commercially available, bisoxazoline ligand. The methodology is straightforward, robust, scalable up to a few grams, and of broad scope allowing the synthesis of a range of β-aryl-carbonyl compounds in good to high enantioselectivities and yields. This new enantioselective Heck-Matsuda arylation allowed the synthesis of β-aryl-γ-lactones and β-aryl aldehydes, which play a vital role as key intermediates in the synthesis of the biologically active compounds, such as (R)-baclofen, (R)-rolipram, (S)-curcumene, (S)-dehydrocurcumene, and (S)-tumerone.
Organocatalytic asymmetric 1,4-addition of organoboronic acids to γ-hydroxy α,β-unsaturated aldehyde: facile synthesis of chiral β-substituted γ-lactones
Kim, Sung-Gon
supporting information; body text, p. 6148 - 6151 (2009/04/05)
Catalytic asymmetric 1,4-addition of arylvinyl- and arylboronic acids to a γ-hydroxy α,β-unsaturated aldehyde, which affords β-substituted γ-lactols, has been established using a diarylprolinol silyl ether as an organocatalyst. The β-substituted γ-lactols have been obtained in good yields and with up to 91% ee, which lead to chiral β-substituted γ-lactones followed by oxidation.
