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- W2065761337 endingPage "8088" @default.
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- W2065761337 abstract "The use of the (S)-α-methylbenzyl group as a chiral auxiliary has allowed the diastereoselective ortho-deprotonation of a chromium tricarbonyl complexed phenoxy ring. When the resultant ortho-anion is treated with an aldehyde two diastereoisomeric complexes are formed, in relatively poor dr, which differ in the configuration of the newly formed benzylic stereogenic centre. However, both ortho-formylation followed by treatment with Grignard reagents and ortho-acylation followed by reduction with Super-Hydride® were found to be completely diastereoselective, giving access to either epimer of the corresponding benzylic alcohol complexes in >99:1 dr. Subsequent oxidative removal of the chromium tricarbonyl unit, followed by cleavage of the O-α-methylbenzyl chiral auxiliary gives enantiopure 2-(1′-hydroxyalkyl)phenols. Following this stereodivergent procedure, either enantiomer of the product may be accessed from a single antipode of [(α-methylbenzyloxy)benzene]Cr(CO)3." @default.
- W2065761337 created "2016-06-24" @default.
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- W2065761337 date "2010-10-01" @default.
- W2065761337 modified "2023-10-16" @default.
- W2065761337 title "The stereodivergent asymmetric synthesis of a range of 2-(1′-hydroxyalkyl)phenols" @default.
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- W2065761337 doi "https://doi.org/10.1016/j.tet.2010.07.058" @default.
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