期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 13, 页码 5159-5163出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b01910
关键词
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资金
- NSFC [21472150, 21871223, 21272002]
- Chongqing Science Technology Commission [cstccxljrc201701, cstc2018jcyjAX0548]
A chiral aldehyde is rationally combined with a Lewis acid and a transition metal for the first time to form a triple catalytic system. This cocatalytic system exhibits good catalytic activation and stereoselective-control abilities in the asymmetric alpha-allylation reaction of N-unprotected amino acid esters and allyl acetates. Optically active alpha,alpha-disubstituted a-amino acids (alpha-AAs) are generated in good yields (up to 87%) and enantioselectivities (up to 96% ee). Preliminary mechanism investigation indicates that the chiral aldehyde 3f acts both as an organocatalyst to activate the amino acid ester via the formation of a Schiff base, and as a ligand to facilitate the nucleophilic attack process by coordinating with pi-allyl Pd(II) species.
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