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Synthesis of Derivatives of the Optically Active β-Amino Acids from (+)-Car-2-ene

✍ Scribed by Ekaterina A. Koneva; Konstantin P. Volcho; Yuri V. Gatilov; Dina V. Korchagina; Georgi E. Salnikov; Nariman F. Salakhutdinov

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
211 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The reaction of (+)‐car‐2‐ene (4) with chlorosulfonyl isocyanate (=sulfuryl chloride isocyanate; ClSO~2~NCO) led to the tricyclic lactams 6 and 8 corresponding to the initial formation both of the tertiary carbenium and α‐cyclopropylcarbenium ions (Scheme 2). A number of optically active derivatives of β‐amino acids which are promising compounds for further use in asymmetric synthesis were synthesized from the lactams (see 16, 17, and 19–21 in Scheme 3).

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