Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between a,b-unsaturated aldehydes and a-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups,...

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Bibliographic Details
Main Authors: Sun, Jun, He, Fangcheng, Wang, Zhongyao, Pan, Dingwu, Zheng, Pengcheng, Mou, Chengli, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
NHC Catalyst
Enantioselectivities
Online Access:https://hdl.handle.net/10356/138269
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Institution: Nanyang Technological University
Language: English
Description
Summary:A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between a,b-unsaturated aldehydes and a-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.

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