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Synthesis of Derivatives of the Optically Active β ‐Amino Acids from (+)‐Car‐2‐ene
Author(s) -
Koneva Ekaterina A.,
Volcho Konstantin P.,
Gatilov Yuri V.,
Korchagina Dina V.,
Salnikov Georgi E.,
Salakhutdinov Nariman F.
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890197
Subject(s) - chemistry , optically active , isocyanate , sulfuryl chloride , chloride , ene reaction , ion , organic chemistry , medicinal chemistry , polyurethane
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 ).