期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 8, 页码 2792-2797出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo200070d
关键词
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资金
- NIDA NIH HHS [R03 DA026960-02, R03 DA026960, R03DA026960] Funding Source: Medline
A series of alpha-amino-1,3-dithianes have been synthesized via the asymmetric Umpolung reaction of 2-lithio-1,3-dithianes with chiral N-phosphonyl imines in good chemical yields (up to 82%) and good to excellent diastereoselectivities (>99:1). The manner by which chiral N-phosphonyl imines are slowly added into the solution of 2-lithio-1,3-dithiane was found to be crucial for achieving excellent diastereoselectivity. The current synthesis was proven to follow the GAP chemistry (group-assistant-purification chemistry) process, which avoids traditional purification techniques of chromatography or recrystallization, i.e., the pure chiral alpha-amino-1,3-dithianes attached with the chiral N-phosphonyl group were readily obtained by washing the solid crude products with hexane or a mixture of hexane ethyl acetate.
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