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Absolute Configuration of 2-Substituted 2-Azabicyclo[2.2.1]hept-5-enes

✍ Scribed by Esteban Pombo-Villar; Jakob Boelsterli; Maria Magdalena Cid; Julien France; Beat Fuchs; Malcolm Walkinshaw; Hans-Peter Weber

Publisher
John Wiley and Sons
Year
1993
Tongue
German
Weight
781 KB
Volume
76
Category
Article
ISSN
0018-019X

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✦ Synopsis

To avoid confusion, it is emphasised that ul and lk refer to additions to a particular face of the corresponding methaniminium ion. Thus, for discussion of the stereoselectivity of this reaction, we shall refer to relative topicity of the addition, rather than to the relative topicity of the products (denoted u and l ) .

The authors thank 0. Hurt and Dr. H.-U. Gremlich for their special efforts in obtaining UV, CD, and IR spectra and Dr. P . Floersheim for structural database searching and collegial discussions.

Experimental Part

General. Solvents and (+)-(R)-cr

-methyl-4-nitrobenzylamine hydrochloride were purchased from Merck, (-)-(S)-l-(4-bromophenyl)ethylamine from Schweizerhall, and the other reagents from Fluka. TLC: Merck silica gel 60 F254 anal. plates; detection by UV or spraying with I* soh. 1, (25 g), KI (20 g), EtOH/H,O 1:4 (1000 ml). M.p.: Biichi-510 melting-point apparatus; in open capillaries; uncorrected. [o(JD: Perkin-Elmer-241 polarimeter; 1-ml microcuvette (I = 10 cm). UVjWS: (Amax [nm] ( E ) ) : Lambda 9. CD (A, , , , [nm] (AE [dm3mol-'cm-']

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