Golden times for allenes: Gold-catalyzed cycloisomerization of beta-hydroxyallenes to dihydropyrans.
The gold(I)-catalyzed 6-endo cycloisomerization of beta-hydroxyallenes provides a mild and efficient access to chiral functionalized dihydropyrans which were obtained at room temperature in good chemical yields with axis-to-center chirality transfer. The method was extended to the beta-aminoallene 12, which afforded tetrahydropyridine 13 in good yield as well.
Gockel
Birgit
B
Organic Chemistry II, Dortmund University, D-44221 Dortmund, Germany.
Krause
Norbert
N
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D011714:Pyrans; C025947:propadiene; D006046:Gold