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200517.fm Page 78 Friday, March 18, 2005 2:52 PM
2005
Cyclopropane derivatives
Q 0021
Dianion Approach to Chiral Cyclopropene Carboxylic Acids. — The dianions of
carboxylic acids are shown to be stable and do not rearrange in contrast
17- 075 cyclopropene
to the corresponding monoanions of their esters. Subsequent capture by electrophiles
provides a general synthesis of 1,2-disubstituted derivatives cyclopropenes. The deprotonation/ alkylation occurs with excellent transfer of absolute stereochemistry as is
shown by example (R)-(Ib). — (LIAO, L.-A.; YAN, N.; FOX*, J. M.; Org. Lett. 6
(2004) 26, 4937-4939; Dep. Chem. Biochem., Univ. Del., Newark, DE 19716, USA;
Eng.) — Steudel
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