α-Lithiation-electrophile trapping of N-thiopivaloylazetidin-3-ol: stereoselective synthesis of 2-substituted 3-hydroxyazetidines.

Journal article

α-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 α-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 α-proton (cis or trans to the hydroxyl group) is initially removed.

Authors: Hodgson, D; Pearson, C; Thompson, A

• Publication status: Published
• Journal: Journal of organic chemistry
• Volume: 78
• Issue: 3
• Pages: 1098-1106
• Publication date: 2013-02-01
• DOI: 10.1021/jo3025225
• EISSN: 1520-6904
• ISSN: 0022-3263
• Language: English
• Keywords: Azetidines; Molecular Structure; Lithium; Stereoisomerism; Protons; Deuterium