Synfacts 2014; 10(1): 0050
DOI: 10.1055/s-0033-1340442
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Enantioselective Synthesis of 1,2-Diols

Rezensent(en):
Mark Lautens
,
Zafar Qureshi
Toribatake K, Nishiyama H * Nagoya University, Japan
Asymmetric Diboration of Terminal Alkenes with a Rhodium Catalyst and Subsequent Oxidation: Enantioselective Synthesis of Optically Active 1,2-Diols.

Angew. Chem. Int. Ed. 2013;
52: 11011-11015
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Publikationsverlauf

Publikationsdatum:
13. Dezember 2013 (online)

 

Significance

Chiral diols are useful synthetic motifs in organic synthesis. Common methods for their synthesis include dihydroxylation, hydrogenation of hydroxyketones, and hydrolysis of epoxides. The authors report an enantioselective 1,2-diboration of alkenes leading to optically active diols after oxidation.


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Comment

Morken showed a similar diboration of terminal alkenes with a platinum catalyst with enantioselectivities up to 94% (J. Am. Chem. Soc. 2009, 131, 13210). The authors present a rhodium-catalyzed diboration–oxidation of terminal alkenes providing enantioselectivities up to 99%. However, disubstituted alkenes proved to be more difficult. 1-Methylstyrene gave the diol with a moderate 76% ee, whereas β-methylstyrene, 1,2-dihydronaphthalene, and trans-stilbene did not react.


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