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2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis

Faraldos, Juan A., Kariuki, Benson and Coates, Robert M. 2011. 2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis. Organic Letters 13 (5) , pp. 836-839. 10.1021/ol1027893

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Abstract

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, cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAlH4 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: ACS
ISSN: 1523-7060
Last Modified: 04 Jun 2017 03:04
URI: http://orca-mwe.cf.ac.uk/id/eprint/16202

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