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- Title
Diastereo‐ and Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols in Two Steps from Terminal Alkynes.
- Authors
Miura, Tomoya; Oku, Naoki; Murakami, Masahiro
- Abstract
We report the highly diastereo‐ and enantioselective preparation of (E)‐δ‐boryl‐substituted anti‐homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)‐catalyzed 1,1‐diboration reaction of terminal alkynes with B2pin2 and a palladium(I)‐mediated asymmetric allylation reaction of the resulting 1,1‐di(boryl)alk‐1‐enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.
- Subjects
ALKYNES; PHOSPHORIC acid; PETROLEUM refining; PALLADIUM; ALDEHYDES; COBALT
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 41, p14762
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201908299