We describe the kinetic resolution of α-silyl-substituted allylboronate esters via chiral phosphoric acid-catalyzed chemo-, diastereo- and enantioselective allylboration of aldehydes. This process provides two synthetically versatile enantioenriched compounds, (Z)-δ-silyl-substituted anti-homoallylic alcohols and α-silyl-substituted allylboronate esters, with a selectivity factor up to 328. We propose that the reaction proceeds through a closed chair-like transition state with the silane moiety occupying a pseudo-axial position, thus readily resolving α-silyl-substituted allylboronate esters. The synthetic utility of the obtained enantioenriched compounds is highlighted by their further transformations to give a diverse set of enantioenriched molecules. (Figure presented.).
|Number of pages||6|
|Journal||Advanced Synthesis and Catalysis|
|Publication status||Published - 2021 Apr 27|
Bibliographical noteFunding Information:
This work was supported by the National Research Foundation of Korea, funded by the Korean government (NRF‐2018R1 A4 A1024713 and NRF2019 M1 A2 A2067940).
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All Science Journal Classification (ASJC) codes
- Organic Chemistry