Kinetic Resolution of a-Silyl-Substituted Allylboronate Esters via Chemo- and Stereoselective Allylboration of Aldehydes
SCIE
SCOPUS
- Title
- Kinetic Resolution of a-Silyl-Substituted Allylboronate Esters via Chemo- and Stereoselective Allylboration of Aldehydes
- Authors
- CHO, SEUNG HWAN; PARK, JIN YOUNG; YONGSUK, JUNG; LEE, EUNSUNG
- Date Issued
- 2021-04
- Publisher
- John Wiley & Sons Ltd.
- Abstract
- We describe the kinetic resolution of alpha-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)-delta-silyl-substituted anti-homoallylic alcohols and alpha-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 alpha-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.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/104540
- DOI
- 10.1002/adsc.202001170
- ISSN
- 1615-4150
- Article Type
- Article
- Citation
- Advanced Synthesis and Catalysis, vol. 363, no. 9, page. 2371 - 2376, 2021-04
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