Phosphine-catalyzed enantioselective synthesis of oxygen heterocycles.
Chiral phosphepine 1 catalyzes the transformation of an array of hydroxy-2-alkynoates into saturated oxygen heterocycles with good enantioselectivity. Phenols are also shown to participate in such phosphine-catalyzed cyclizations, including an asymmetric variant. This method provides a new approach to the enantioselective synthesis of tetrahydrofurans, tetrahydropyrans, and dihydrobenzopyrans.
Chung
Ying Kit
YK
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Fu
Gregory C
GC
D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D002839:Chromans; D005663:Furans; D006571:Heterocyclic Compounds; D010720:Phosphines; D011714:Pyrans; C044646:phosphine; D010100:Oxygen