TY - JOUR
T1 - The grignard reaction of Cyclodextrin 6-aldehydes revisited
T2 - a study of the stereoselectivity upon addition of organometallic reagents to aldehydes and ketones.
AU - Lindbäck, Emil Anders
AU - Zhou, You
AU - Marinescu-Pedersen, Lavinia G
AU - Pedersen, Christian Marcus
AU - Bols, Mikael
PY - 2010/7
Y1 - 2010/7
N2 - 2A-G, 3A-G, 6B-G -Icosakis-O-benzyl-6 A-O-oxo-ß-cyclodextrin was treated with aromatic and aliphatic Grignard reagents to give diastereomeric mixtures of the secondary alcohols with remarkable difference in polarity. Moderate-to-good yields and selectivity were obtained. By oxidizing the secondary alcohols, followed by a second Grignard reaction, good to excellent yields and selectivity of tertiary alcohols could be obtained. The stereochemistry of the reaction outcome was shown to be dependent on the order of addition of the Grignard reagents and could be efficiently controlled.
AB - 2A-G, 3A-G, 6B-G -Icosakis-O-benzyl-6 A-O-oxo-ß-cyclodextrin was treated with aromatic and aliphatic Grignard reagents to give diastereomeric mixtures of the secondary alcohols with remarkable difference in polarity. Moderate-to-good yields and selectivity were obtained. By oxidizing the secondary alcohols, followed by a second Grignard reaction, good to excellent yields and selectivity of tertiary alcohols could be obtained. The stereochemistry of the reaction outcome was shown to be dependent on the order of addition of the Grignard reagents and could be efficiently controlled.
U2 - 10.1002/ejoc.201000295
DO - 10.1002/ejoc.201000295
M3 - Journal article
SN - 1434-193X
VL - 2010
SP - 3883
EP - 3896
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 20
ER -