Phosphine-catalyzed domino reaction: highly stereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and allylic carbonates.
A novel phosphine-catalyzed domino reaction of salicyl N-thiophosphinyl imines and allylic carbonates was developed. The allylic carbonate, in this reaction, serves as a new kind of 1,1-dipolar synthon. This method offered a powerful approach to the construction of a highly substituted trans-2,3-dihydrobenzofuran skeleton with high diastereoselectivity.
Xie
Peizhong
P
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
Huang
You
Y
Chen
Ruyu
R
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D012459:Salicylates / Q000737:chemistry*; D013237:Stereoisomerism
D001572:Benzofurans; D002254:Carbonates; D007097:Imines; D010720:Phosphines; D012459:Salicylates; C044646:phosphine