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2005
Cyclopentane derivatives
Q 0030
Aryl- and Alkenyllithium Preparations and Copper-Catalyzed Reaction Between
Derived Magnesium Reagents and the Monoacetate of 4-Cyclopentene33- 080 the
-1,3-diol. — The CuCN-catalyzed substitution reaction of cyclopentene (I) with
aryl-MgCl to afford the SN2 products includes aryl and alkenyllithium anions. They
are prepared through halogen—lithium exchange with lithium, exchange with t-BuLi,
stannane—lithium exchange with BuLi, and direct lithiation with BuLi. The lithium
anion prepared by the usual halogen—lithium exchange with BuLi is not compatible
with the CuCN-catalyzed reaction. The methodology is applied to various product
types including the prostaglandin precursor (XIII). — (NAKATA, K.; KOBAYASHI*,
Y.; Org. Lett. 7 (2005) 7, 1319-1322; Dep. Biomol. Eng., Tokyo Inst. Technol.,
Midori, Yokohama 226, Japan; Eng.) — R. Steudel
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