TY - JOUR
T1 - Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols
T2 - Protecting-Group-Free Synthesis of Substituted Pyrans
AU - Shin, Inji
AU - Wang, Gang
AU - Krische, Michael J.
N1 - Publisher Copyright:
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2014/10/1
Y1 - 2014/10/1
N2 - The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.
AB - The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.
KW - catalyst-directed diastereoselectivity
KW - polyketides
KW - protecting group-free reactions
KW - pyran
KW - transfer hydrogenation
UR - http://www.scopus.com/inward/record.url?scp=84941032064&partnerID=8YFLogxK
U2 - 10.1002/chem.201404065
DO - 10.1002/chem.201404065
M3 - Article
C2 - 24771318
AN - SCOPUS:84941032064
SN - 0947-6539
VL - 20
SP - 13382
EP - 13389
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 41
ER -