期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 43, 页码 15608-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja907711a
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资金
- University of Toronto
- Canada Foundation for Innovation
- Ontario Research Fund
- National Science and Engineering Council of Canada (NSERC)
- Boehringer Ingelheim (Canada) Ltd
Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key rote counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.
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