Synfacts 2011(8): 0903-0903  
DOI: 10.1055/s-0030-1260836
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Assembly of Complex Molecules via Dearomatization-Catalytic Desymmetrization

Contributor(s): Benjamin List, Ji-Woong Lee
R. Leon, A. Jawalekar, T. Redert, M. J. Gaunt*
University of Cambridge, UK
Weitere Informationen


20. Juli 2011 (online)


The authors developed a straightforward procedure to access complex molecules 1 via electrophile-triggered dearomatization and catalytic desymmetrization of the meso-intermediate A. The obtained tricyclic compounds possess three contiguous stereocenters, one quaternary and two tertiary ones. Also, compounds 1 contain various functional groups (i.e. aldehyde, enone, ­vinyl iodide), which could be utilized to transform it into more complex molecules. Moreover, the N-methyl propargyl amide which has an aldehyde in the same chain gave a constitutionally different tricyclic compound with high enantioselectivity.