期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 30, 页码 9774-9780出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b06676
关键词
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资金
- NSFC [21472150]
- Program for New Century Excellent Talents in Universities [NCET-12-0929]
- National Key Research and Development Program of China [2018YFA0507900]
Chiral aldehyde catalysis is uniquely suitable for the direct asymmetric alpha-functionalization of N-unprotected amino acids, because aldehydes can reversibly form imines. However, there have been few successful reports of these transformations. In fact, only chiral aldehyde catalyzed aldol reactions of amino acids and alkylation of 2-amino malonates have been reported with good chiral induction. Here, we report a novel type of chiral aldehyde catalyst based on face control of the enolate intermediates. The resulting chiral aldehyde is the first efficient nonpyridoxal-dependent catalyst that can promote the direct asymmetric alpha-functionalization of N-unprotected glycine esters. Possible transition states and the proton transfer process were investigated by density functional theory calculations.
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