Asymmetric C(sp)–H Addition of Terminal Alkynes to Cyclopropenes by a Chiral Gadolinium Catalyst

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 a...

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Bibliographic Details
Published in:ACS catalysis 2018-05, Vol.8 (5), p.4705-4709
Main Authors: Teng, Huai-Long, Ma, Yuanhong, Zhan, Gu, Nishiura, Masayoshi, Hou, Zhaomin
Format: Article
Language:English
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Summary: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C moiety has also been demonstrated to give further diversified chiral cyclopropane derivatives which are otherwise difficult to access.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b01189