期刊
TETRAHEDRON
卷 67, 期 36, 页码 6953-6959出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.042
关键词
Chiral dipeptides; Organocatalysis; Ball-milling; Green chemistry; Asymmetric aldol reaction
资金
- Conacyt, Mexico [60366-Q, 22211]
The organocatalytic activity of (S)-proline-based dipeptides 1a-c has been evaluated in the asymmetric aldol reaction between representative ketones with various aromatic aldehydes under solvent-free conditions in a ball mill. In particular, the methyl ester of (S)-proline-(S)-tryptophan, (S,S)-1c, proved to be an efficient organocatalyst, and the aldol reaction proceeded with good chemical yields and excellent diastereo- and enantioselectivity (up to 98:2 anti/syn dr and up to 98% ee), in the presence of water, and 5 mol % of benzoic acid as additive. (C) 2011 Elsevier Ltd. All rights reserved.
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