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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.


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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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