Copper-Catalyzed Diastereoselective Addition of Diborylmethane to N-tert-Butanesulfinyl Aldimines: Synthesis of β-Aminoboronates
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- Title
- Copper-Catalyzed Diastereoselective Addition of Diborylmethane to N-tert-Butanesulfinyl Aldimines: Synthesis of β-Aminoboronates
- Authors
- Jinyoung Park; Yeosan Lee; Junghoon Kim; Cho, SH
- Date Issued
- 2016-03-04
- Publisher
- American Chemical Society
- Abstract
- We have developed a highly chemo- and diastereoselective alkylation of N-tert-butanesulfinyl aldimines with diborylmethane. Whereas the addition of diborylmethane under metal-free conditions shows poor diastereoselectivity, the use of a copper catalyst and a bidentate phosphine ligand significantly enhances the diastereoselectivity, providing chiral beta-aminoboronates in good yields. On the basis of the stereochemical outcome, we propose that the reaction likely proceeds via a boron-chelating six-membered chairlike transition state.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/36987
- DOI
- 10.1021/ACS.ORGLETT.6B00376
- ISSN
- 1523-7060
- Article Type
- Article
- Citation
- Organic Letters, vol. 18, no. 5, page. 1210 - 1213, 2016-03-04
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