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Asymmetric [3+2] Cycloaddition Reactions of α‐Substituted Diazophosphonates with 3‐Acryloyl‐2‐oxazolidinone to Access Chiral Pyrazoline Derivatives with Phosphonyl at a Tetrasubstituted Stereogenic Center
Author(s) -
Huang Nan,
Tong Xunfei,
Zhou Surong,
Guo Qixiang,
Peng Yungui
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900679
Subject(s) - stereocenter , chemistry , cycloaddition , phosphonate , pyrazoline , stereochemistry , bicyclic molecule , combinatorial chemistry , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis
An efficient asymmetric 1,3‐dipolar cycloaddition reaction between α ‐substituted diazophosphonates and 3‐acryloyl‐2‐oxazolidinone, catalyzed by a chiral Mg(II)/BOX complex, has been achieved for the first time. This reaction gave the corresponding chiral 5,5‐disubstituted 1 H ‐pyrazoline‐5‐phosphonates in good yields (up to 98%) and excellent stereoselectivities (up to 95% ee ). The resulting highly functionalized pyrazolines, which have a tetrasubstituted stereogenic center at the phosphonate‐bearing carbon, can be further transformed into pyrazolidine and bicyclic pyrazolidine derivatives.