Using 1 -chloro-l-[~~N]nitrosocyclohexane, we have prepared five L-[a-'SN]arnino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-l0,2-suftams, followed by ZnO/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5 % e.e. By starti
✦ LIBER ✦
The preparation of tobacco constituents incorporating stable isotopes, I. The synthesis of d,l-nornicotine-1′-15N and d,l-nicotine-1′-15N
✍ Scribed by William B. Edwards III; David F. Glenn; Frank Green; R. H. Newman
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- French
- Weight
- 239 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
Isotopically enriched d,l‐nornicotine‐1^1^‐^15^N (24 atom % enrichment) was prepared in a single step from cyclopropyl 3‐pyridyl ketone and formamide‐^15^N (24 atom % enrichment). Methylation to d,l‐nicotine‐1^1^‐^15^N (24 atom % enrichment) was accomplished using the Clark‐Eschweiler method.
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