Journal
ACS CATALYSIS
Volume 8, Issue 5, Pages 4705-4709Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b01189
Keywords
alkynylcyclopropane; asymmetric catalysis; hydroalkynylation; cyclopentadienyl ligand; half-sandwich complex; lanthanide; rare earth metal
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Funding
- JSPS [26220802, 17H06451]
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We herein report the diastereo- and enantioselective C(sp)-H addition of terminal alkynes to cyclopropenes by a chiral half-sandwich gadolinium catalyst. This protocol constitutes the first example of asymmetric hydroalkynylation of cyclopropenes with terminal alkynes and offers a straightforward and 100% atom-efficient route for the synthesis of a wide range of enantioenriched alkynylcyclopropane derivatives in high yields (65-96%) and excellent stereoselectivity (>20:1 dr; 90-99% ee). Elaboration of some of the alkynylcyclopropane products through selective transformation of the C equivalent to C moiety has also been demonstrated to give further diversified chiral cyclopropane derivatives which are otherwise difficult to access.
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