期刊
ORGANIC LETTERS
卷 18, 期 5, 页码 1210-1213出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00376
关键词
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资金
- Basic Science Research Program through the National Research Foundation of Korea (NRF) - Ministry of Science, ICT & Future Planning [NRF-2015R1C1A1A02036326]
- National Research Foundation of Korea [10Z20130000001] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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.
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