Enantioselective 1,6‐Conjugate Addition of Dialkyl α‐Diazo Methylphosphonate to para‐Quinone Methides

An asymmetric 1,6‐conjugate addition reaction of dialkyl diazomethylphosphonates to para‐quinone methides promoted by phase‐transfer catalysis has been developed. A series of chiral diarylmethylated diazomethylphosphonates were accessed with up to 85% yields and 99% ee enantioselectivities. The resu...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-11, Vol.363 (21), p.4856-4861
Main Authors: Chen, Yuan, Yu, Rui, Wang, Min, Huang, Yanmin, Peng, Yungui
Format: Article
Language:English
Subjects:
Asymmetric catalysis
conjugate addition
Conjugates
dihydrocinnoline phosphonate
Enantiomers
para-quinone methide
Phosphonates
Quinones
α-diazo methylphosphonate
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Summary:An asymmetric 1,6‐conjugate addition reaction of dialkyl diazomethylphosphonates to para‐quinone methides promoted by phase‐transfer catalysis has been developed. A series of chiral diarylmethylated diazomethylphosphonates were accessed with up to 85% yields and 99% ee enantioselectivities. The resulting products were further transformed into bioactive compounds, namely, a chiral dihydrocinnoline phosphonate and a chiral α‐aminophosphonate, bearing diarylmethine stereogenic centers.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100881