Deuterium as a Stereochemically Invisible Blocking Group for Chiral Ligand Synthesis

Ross A. Arthurs, Christopher J. Richards

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)
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Abstract

Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).

Original languageEnglish
Pages (from-to)702-705
Number of pages4
JournalOrganic Letters
Volume19
Issue number3
Early online date24 Jan 2017
DOIs
Publication statusPublished - 3 Feb 2017

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