Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration |
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| Authors: | Yao-Jun Shi David L HughesJames M McNamara |
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| Institution: | Department of Process Research, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065 USA |
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| Abstract: | Mitsunobu reaction of chiral tertiary alcohol (S)-2 with phenol 3 provides the desired ether (R)-1 in moderate yields at elevated temperatures (80-100°C). The SN2 displacement pathway is evident by complete inversion of the (S)-alcohol to (R)-ether. |
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| Keywords: | Mitsunobu reaction tertiary alcohols alkyl aryl ether SN2 displacement inversion |
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