Chemoselectivity of the Ru-catalyzed cycloisomerization reaction for the synthesis of dihydropyrans; application to the synthesis of L-forosamine.
The chemoselectivity of a Ru-catalyzed cycloisomerization reaction has been established. The preference for O- capture of the vinylidene intermediate allows for the synthesis of 4-aminodihydropyrans that are valuable synthetic intermediates. The synthetic utility of these structures has been demonstrated in the synthesis of l-forosamine.
Zacuto
Michael J
MJ
Department of Process Research, Merck and Co., Inc., Rahway, New Jersey 07065, USA. michael_zacuto@merck.com
Tomita
Daisuke
D
Pirzada
Zainab
Z
Xu
Feng
F
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D006595:Hexosamines; D011714:Pyrans; C012325:forosamine; D012428:Ruthenium