Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors
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چکیده
منابع مشابه
Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors
The copper-catalyzed asymmetric conjugate addition (ACA) of nucleophiles onto polyenic Michael acceptors represents an attractive and powerful methodology for the synthesis of relevant chiral molecules, as it enables in a straightforward manner the sequential generation of two or more stereogenic centers. In the last decade, various chiral copper-based catalysts were evaluated in combination wi...
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Conjugate addition (1,4-addition) of carbon nucleophiles to a; b-unsaturated compounds is one of the most important carbon–carbon bond-forming strategies in synthetic organic chemistry [1]. The versatility of the conjugate addition is mainly due to the large variety of nucleophiles (organometallic reagents, Michael donors, other carbanions) and acceptors (a; b-unsaturated aldehydes, ketones, ni...
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Chiral framework: Chiral amines with pyrrolidine frameworks catalyze the enantioselective conjugate addition of a wide range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99 % ee (see scheme). The high versatility of the Michael adducts is exemplified by various functionalizations with conservation of the optical purity.Chiral ...
متن کاملCopper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones.
It is no longer necessary to use dialkylzinc reagents to obtain enantioselectivities >95% in the copper-catalyzed asymmetric conjugate addition of organometallic compounds to cyclic enones. We now report how this can be accomplished by using inexpensive and readily available Grignard reagents. Screening of bidentate ligands provided outstanding results with copper complexes of commercially avai...
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The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol%) of a copper(I)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne. Pre-metalation of the terminal 1,3-diyne with stoichiometric or higher amounts of dialkylzinc reagent is not required. The corresponding internal diynes bearing a propargylic stereogenic c...
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ژورنال
عنوان ژورنال: Beilstein Journal of Organic Chemistry
سال: 2020
ISSN: 1860-5397
DOI: 10.3762/bjoc.16.24