Download PDF
Synfacts 2006(9): 0954-0954  
DOI: 10.1055/s-2006-949229
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Clerodane-Derivatives by Catalytic Morita-Baylis-Hillman Reaction

Contributor(s): Benjamin List, Sonja Mayer
S. A. Rodgen, S. E. Schaus*
Boston University, USA
Further Information

Publication History

Publication Date:
23 August 2006 (online)

    Permissions and Reprints

Significance

The decalin core 5 of asmarine A (6) has been synthesized, employing binaphthol derivative 1 as general Brønsted acid catalyst for a highly diastereoselective asymmetric Morita-Bay­lis-Hillman (MBH) reaction followed by an intramolecular Hosomi-Sakurai reaction. Starting from silane-containing aldehydes 3 and cyclohexenone 2, MBH products 4 could be obtained in good yields (75-97%) and high enantiomeric ratios (from 93:7 to 99:1) with 1 as the catalyst under mild conditions.