期刊
ORGANIC LETTERS
卷 13, 期 5, 页码 836-839出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol1027893
关键词
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资金
- NIH [GM 13956]
The enantiomeric 2-azapinanes, aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (-)- and (+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement of the pinonic acid oximes(1) cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAIH(4) reductions. The anti stereochemistry of the N-methyl groups in the salts with respect to the gem-dimethyl bridge was established by NOE measurements and by X-ray diffraction analysis.
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