alpha-Lithiation-Electrophile Trapping of N-Thiopivaloylazetidin-3-ol: Stereoselective Synthesis of 2-Substituted 3-Hydroxyazetidines

作者：Hodgson David M^*; Pearson Christopher I; Thompson Amber L

来源：Journal of Organic Chemistry, 2013, 78(3): 1098-1106.

DOI：10.1021/jo3025225

alpha-Lithiation of N-thiopivaloylazetidin-3-ol and subsequent electrophile trapping provides access to a range of 2-substituted 3-hydroxyazetidines with generally good trans-diastereoselectivity, aside from deuteration, which gives the cis-diastereoisomer. Deuterium labeling studies indicate that the initial alpha-deprotonation occurs preferentially, but not exclusively, in a trans-selective manner. These studies also suggest that the stereochemical outcome of the electrophile trapping depends on the electrophile used but is independent of which alpha-proton (cis or trans to the hydroxyl group) is initially removed.

• 出版日期2013-2-1