Bifunctional phosphine-catalyzed domino reaction: highly stereoselective synthesis of cis-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and allenes.
A new bifunctional phosphine catalyst, (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (LBBA-1), was developed for the highly stereoselective synthesis of cis-2,3-dihydrobenzofurans via an aza-Morita-Baylis-Hillman/umpolung addition domino reaction of salicyl N-thiophosphinyl imines with electron-deficient allenes. Dual activation of both nucleophile and electrophile by the bifunctional catalyst accounts for the observed high reactivity and stereoselectivity.
Meng
Xiangtai
X
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
Huang
You
Y
Chen
Ruyu
R
D000466:Alkadienes / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
C534972:(2'-hydroxybiphenyl-2-yl)diethylphosphane; D000466:Alkadienes; D001572:Benzofurans; D001713:Biphenyl Compounds; D007097:Imines; D010720:Phosphines; C043168:coumaran