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Synfacts 2019; 15(02): 0147
DOI: 10.1055/s-0037-1611997
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Diastereo- and Enantioselective Conjunctive Cross-Coupling via a Metalate Shift

Contributor(s):
Mark Lautens
,
José F. Rodríguez
Myhill JA, Wilhelmsen CA, Zhang L, Morken JP. * Boston College, USA
Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design.

J. Am. Chem. Soc. 2018;
140: 15181-15185
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Further Information

Publication History

Publication Date:
18 January 2019 (online)

 
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Key words

palladium catalysis - conjunctive cross-coupling - metalate shift

Significance

The authors describe a conjunctive cross-coupling process to access products with vicinal stereogenic centers. This method avoids the generation of Suzuki–Miyaura stilbene byproducts obtained when typical boronic esters are employed.


 

Comment

Products are obtained in moderate yields and excellent enantio- and diastereoselectivities. The synthetic utility of the –B(mac) handle is demonstrated. Additionally, this methodology was used for the synthesis of (+)-obtusafuran.


 

 


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