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200517.fm Page 79 Friday, March 18, 2005 2:52 PM
2005
Cyclopropane derivatives
Q 0021
Efficient Synthesis of Enantiomerically Pure α-Alkyl Cyclopropanecarbonitrile
from Pyrazolines. — One of the most efficient methods for synthesizing
17- 076 Derivatives
optically pure cyclopropanes and alkylidenecyclopropanes containing a quaternary
chiral center is described. Key step is the thermal extrusion of nitrogen from chiral
pyrazolines, which contain a quaternary carbon (C-3) bearing an electron-withdrawing
cyano group. The extrusion takes place in very high yields with complete retention of
the configuration of all the chiral centers. — (GARCIA RUANO*, J. L.; ALONSO
DE DIEGO, S. A.; MARTIN, M. R.; TORRENTE, E.; MARTIN CASTRO, A. M.;
Org. Lett. 6 (2004) 26, 4945-4948; Dep. Quim. Org., Univ. Auton., Cantoblanco,
E-28049 Madrid, Spain; Eng.) — Steudel
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