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1.
Org Lett ; 16(12): 3288-91, 2014 Jun 20.
Article in English | MEDLINE | ID: mdl-24893570

ABSTRACT

The asymmetric synthesis of ß-substituted lactones by catalytic asymmetric conjugate addition of alkyl groups to α,ß-unsaturated lactones is reported. The method uses alkylzirconium nucleophiles prepared in situ from alkenes and the Schwartz reagent. Enantioselective additions to 6- and 7-membered lactones proceed at rt, tolerate a wide variety of functional groups, and are readily scalable. The method was used in a formal asymmetric synthesis of mitsugashiwalactone.

2.
J Am Chem Soc ; 134(41): 16955-8, 2012 Oct 17.
Article in English | MEDLINE | ID: mdl-22998336

ABSTRACT

A rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines has been developed. High enantioselectivities have been achieved by employing (S,S)-Me-Duphos as the ligand through "enantioselective transmetalation".


Subject(s)
Organometallic Compounds/chemistry , Rhodium/chemistry , Silicon Compounds/chemical synthesis , Silicon/chemistry , Catalysis , Crystallography, X-Ray , Molecular Structure , Silicon Compounds/chemistry , Stereoisomerism
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