TY - JOUR
T1 - 2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity
AU - Yasomanee, Jagodige P.
AU - Parameswar, Archana R.
AU - Pornsuriyasak, Papapida
AU - Rath, Nigam P.
AU - Demchenko, Alexei V.
N1 - 2-O-Picolinyl protected glycosyl donors lead to the formation of 1,2-trans glycosides with complete stereoselectivity. This is due to the participatory effect of the picolinyl nitrogen that is able to block the bottom face of the ring via a six-membered cyclic intermediate. Herein we demonstrate that if the
PY - 2016/1/1
Y1 - 2016/1/1
N2 - 2- O -Picolinyl protected glycosyl donors lead to the formation of 1,2- trans glycosides with complete stereoselectivity. This is due to the participatory effect of the picolinyl nitrogen that is able to block the bottom face of the ring via a six-membered cyclic intermediate. Herein we demonstrate that if the nitrogen atom of the O -picolinyl moiety is temporarily blocked by coordination to the metal center (Pd), it becomes unavailable to participate in glycosylation and hence the stereoselectivity of 2- O -picolinyl-assisted glycosylations can be “switched”.
AB - 2- O -Picolinyl protected glycosyl donors lead to the formation of 1,2- trans glycosides with complete stereoselectivity. This is due to the participatory effect of the picolinyl nitrogen that is able to block the bottom face of the ring via a six-membered cyclic intermediate. Herein we demonstrate that if the nitrogen atom of the O -picolinyl moiety is temporarily blocked by coordination to the metal center (Pd), it becomes unavailable to participate in glycosylation and hence the stereoselectivity of 2- O -picolinyl-assisted glycosylations can be “switched”.
UR - https://pubs.rsc.org/en/content/articlelanding/2016/ob/c6ob00107f
UR - https://doi.org/10.1039/C6OB00107F
U2 - 10.1039/C6OB00107F
DO - 10.1039/C6OB00107F
M3 - Article
VL - 14
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
ER -