Cinchona–Diaminomethylenemalononitrile Organocatalyst for the Highly Enantioselective Hydrophosphonylation of Ketones and Enones

The use of diaminomethylenemalononitrile (DMM) organocatalyst to promote the challenging 1,2-hydrophosphonylation of simple ketones and enones, which are also called α,β-unsaturated ketones, is proposed and validated. This reaction provided the corresponding chiral α-hydroxy phosphonates in high to...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (18), p.5569-5572
Main Authors: Arai, Ryoga, Hirashima, Shin-ichi, Kondo, Junko, Nakashima, Kosuke, Koseki, Yuji, Miura, Tsuyoshi
Format: Article
Language:English
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Summary:The use of diaminomethylenemalononitrile (DMM) organocatalyst to promote the challenging 1,2-hydrophosphonylation of simple ketones and enones, which are also called α,β-unsaturated ketones, is proposed and validated. This reaction provided the corresponding chiral α-hydroxy phosphonates in high to excellent yields and with enantioselectivity up to 96% ee.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02241