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Recent developments in the synthesis of helicene-like molecules.
  • A. Urbano
  • Chemistry
    Angewandte Chemie
  • 5 September 2003
The pioneering work of Katz and Liu led to the production of racemic helicene bisquinones through a Diels–Alder approach (Scheme 1), supplemented by an efficient procedure for effecting the required resolutions.
Enantioselective total synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC [(S)-LLU-alpha].
The key step is a stereoselective TiCl(4)-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.
Enantiopure sulfoxides: recent applications in asymmetric synthesis.
Significant recent advances leading to high asymmetric inductions in carbon-carbon and carbon-oxygen bond forming reactions, and applications of homochiral sulfoxides to atroposelective synthesis and asymmetric catalysis are discussed.
Reductive cyclizations of hydroxysulfinyl ketones: enantioselective access to tetrahydropyran and tetrahydrofuran derivatives.
The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofuran-2-yl)acetic acid is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization of the resulting hydroxysulfinyl ketones.
Enantioselective synthesis of helicenequinones and -bisquinones.
A convergent approach based on Diels-Alder reactions between polycyclic dienes and benzoquinones has emerged as a powerful tool for the construction of helicenequinones and bisquinones. Chemical
Efficient asymmetric synthesis of [7]helicene bisquinones.
The efficient one-pot six-step domino process which occurs when (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1) reacts with 3,6-divinyl-1,2,7,8-tetrahydrophenanthrenes 2a-c allowed enantioselective