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Synfacts 2019; 15(04): 0395
DOI: 10.1055/s-0037-1612349
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Enantioselective Reduction of α,β-Unsaturated Esters

Contributor(s):
Mark Lautens
,
José F. Rodríguez
Appella DH, Moritani Y, Shintani R, Ferreira EM, Buchwald SL. * Massachusetts Institute of Technology, Cambridge, USA
Asymmetric Conjugate Reduction of α,β-Unsaturated Esters Using a Chiral Phosphine–Copper Catalyst.

J. Am. Chem. Soc. 1999;
121: 9473-9474
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Further Information

Publication History

Publication Date:
19 March 2019 (online)

 
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Key words

copper catalysis - conjugate reduction - silanes

Significance

Buchwald and co-workers reported the use of copper and chiral bisphosphine ligands for the enantioselective 1,4-reduction of α,β-unsaturated esters. Polymethylhydroxiloxane (PMHS) was employed as a stoichiometric hydride source.


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Comment

Novel methodologies have been developed since this seminal report on the enantioselective hydrofunctionalization of alkenes. Use of DTBM-SEGPHOS as the ligand and other hydride sources are now available for the asymmetric reduction of less activated alkenes.


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