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Synfacts 2014; 10(3): 0276
DOI: 10.1055/s-0033-1340691
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Asymmetric Allylic Alkylation of Ketones

Contributor(s):
Hisashi Yamamoto
,
Fengtao Zhou
Li X.-H, Zheng B.-H, Ding C.-H, Hou X.-L * Shanghai Institute of Organic Chemistry, P. R. of China
Enantioselective Synthesis of 2,3-Disubstituted Indanones via Pd-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Ketones.

Org. Lett. 2013;
15: 6086-6089
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Publication History

Publication Date:
17 February 2014 (online)

 
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Key words

allylic alkylation - ketones - indanones - palladium

Significance

Disubstituted indanones represent important structural motifs in natural products and pharmaceuticals. However, methods for the enantioselective synthesis of these structures are limited. Hou and co-workers report the asymmetric synthesis of disubstituted indanones in good yield and high enantio- and diastereoselectivities via palladium-catalyzed intramolecular allylic alkylation of ketones.


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Comment

Interestingly, the use of the solvent mixture tert-butanol–2-methoxyethanol resulted in higher enantio- and diastereoselectivity. Furthermore, it is easy to transform these optically active disubstituted indanones into other important subunits of natural products.


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