Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 23, Pages 9518-9521Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8021956
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [19020020]
- Grants-in-Aid for Scientific Research [19020020] Funding Source: KAKEN
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Highly efficient sequential addition reactions of organolithium and -magnesium reagents to N-thioformyl 2-methoxymethylpyrrolidine have been described. Various combinations of these reagents gives successful results. A highly efficient and diastereoselective addition reaction is also described. Use of the opposite combinations of substituents on organolithium and -magnesium reagents leads to the selective formation of the opposite diastereomers. The reaction was extended to N-thioformyl 2-siloxymethypyrrolidine and 2-methoxymethylpiperidine, and these showed similar efficiency and selectivity.
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