TY - JOUR
T1 - Palladium/zinc co-catalyzed syn-stereoselectively asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols
AU - Li, Sifeng
AU - Xu, Jianbin
AU - Fan, Baomin
AU - Lu, Zhiwu
AU - Zeng, Chaoyuan
AU - Bian, Zhaoxiang
AU - Zhou, Yongyun
AU - Wang, Jun
N1 - Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/6/1
Y1 - 2015/6/1
N2 - A new palladium/zinc co-catalyst system associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols is reported. This catalyst system allows the formation of cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95-% yield) with excellent enantioselectivities (up to 99-% ee). The cis-configuration of the product has been confirmed by X-ray crystal structure analysis. To the best of our knowledge, it represents the first example in ring-opening reactions of bicycloalkenes with heteronucleophiles in a syn-stereoselective manner. Open the ring: A new palladium/zinc co-catalyst associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenolic or naphtholic nucleophiles was developed, which afforded the corresponding cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95-% yield) with excellent enantioselectivities (up to 99-% ee).
AB - A new palladium/zinc co-catalyst system associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols is reported. This catalyst system allows the formation of cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95-% yield) with excellent enantioselectivities (up to 99-% ee). The cis-configuration of the product has been confirmed by X-ray crystal structure analysis. To the best of our knowledge, it represents the first example in ring-opening reactions of bicycloalkenes with heteronucleophiles in a syn-stereoselective manner. Open the ring: A new palladium/zinc co-catalyst associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenolic or naphtholic nucleophiles was developed, which afforded the corresponding cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95-% yield) with excellent enantioselectivities (up to 99-% ee).
KW - asymmetric catalysis
KW - oxabenzonorbornadienes
KW - phenols
KW - ring-opening reaction
KW - syn-stereoselectivity
UR - http://www.scopus.com/inward/record.url?scp=84930651013&partnerID=8YFLogxK
U2 - 10.1002/chem.201500816
DO - 10.1002/chem.201500816
M3 - Journal article
AN - SCOPUS:84930651013
SN - 0947-6539
VL - 21
SP - 9003
EP - 9007
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 25
ER -