What question did this study set out to answer?

To develop a catalytic enantioselective reaction sequence for the net asymmetric carbohydroxylation of alkenes in a single reaction vessel.

November 27, 2003Organic Letters

Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction

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Authors

SMSteven P. MillerMerck & Co., Inc., Rahway, NJ, USA (United States)JMJeremy B. MorganUniversity of North Carolina Wilmington FNFelix J. NepveuxTufts University

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Implication

Experimental study demonstrates asymmetric carbohydroxylation of alkenes via a tandem reaction, suggesting an efficient one-pot synthesis of chiral alcohols.

Key Points

To develop a catalytic enantioselective reaction sequence for the net asymmetric carbohydroxylation of alkenes in a single reaction vessel.
Generated chiral nonsymmetric 1,2-diboron adducts via catalytic enantioselective diboration of alkenes.
Conducted in situ Suzuki cross-coupling of 1,2-diboron intermediates with aryl halides at the less hindered carbon-boron bond.
Carried out oxidative workup to convert the remaining carbon-boron bond into a hydroxyl group.
Direct oxidation of the generated chiral 1,2-diboron adducts yielded 1,2-diols in good yield.
The sequential one-pot diboration, Suzuki cross-coupling, and oxidation enabled successful net asymmetric carbohydroxylation of alkenes.

Cite This Study

Miller et al. (2003) studied this question.

synapsesocial.com/papers/69e5b6493320d84e697f89c7 https://doi.org/10.1021/ol036219a

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Implication

Experimental study demonstrates asymmetric carbohydroxylation of alkenes via a tandem reaction, suggesting an efficient one-pot synthesis of chiral alcohols.

Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction

Discussion

Member takes

Implication

Key Points

Cite This Study

Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction

Discussion

Member takes

Implication

Key Points

Cite This Study

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