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Synfacts 2007(2): 0177-0177  
DOI: 10.1055/s-2006-955845
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Pd(II)-Catalyzed Addition of Malonates to Dihydroisoquinolines

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
N. Sasamoto, C. Dubs, Y. Hamashima, M. Sodeoka*
Tohoku University, Wako, Japan
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

This is a nice report of the synthesis of C1-chiral tetrahydroisoquinolines (THIQs) from dihydroisoquinolines (DHIQs). DM-SEGPHOS (1) was found to be the best ligand for this reaction and the order of addition of reactants was also found to be important. Interestingly, addition of Boc anhydride to the DHIQ followed by the catalyst and the malonate nucleophile proved the necessary order of addition for any conversion. Isopropyl malonate was found to be the best nucleophile, giving high conversion and high ee values. A variety of substituted DHIQs gave high yields and good enantioselectivities with isopropyl malonate.