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

• 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
• Institution: Nanyang Technological University

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.