Stereoconvergent Generation of a Contrasteric syn-Bicyclopropylidene (=syn-Cyclopropylidenecyclopropane) by Stille-Like Coupling
Özet
Stereoisomerically pure endo- and exo-7-halo-7-(trimethylstannyl)benzonorcar-3-enes (=endo- and exo-(1-halo-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-1-yl)trimethylstannane) 4 and 6 were selectively obtained by lithiumtin or magnesiumtin transmetalation in good yields (Scheme2 and 3). The reaction of these compounds with copper(I) thiophene-2-carboxylate (CuTC) produced in both cases the corresponding CS-symmetric bicyclopropylidene (=cyclopropylidenecyclopropane) syn-1, a single diastereoisomer (Schemes5 and 6). The structure of syn-1 was undoubtedly elucidated by X-ray single crystal diffraction. The coupling mechanism of the carbenoid cyclopropane is discussed (Scheme7).
Atıf için künye
Guney, M., Essiz, S., Daştan, A., Balci, M., DE LUCCHI, O., Şahin, E., & FABRIS, F. (2013). Stereoconvergent Generation of a Contrasteric syn-Bicyclopropylidene (=syn-Cyclopropylidenecyclopropane) by Stille-Like Coupling. HELVETICA CHIMICA ACTA, 96(5), 941–950. https://doi.org/10.1002/hlca.201200291
BibTeX
@article{guney2013-66769,
author = {Guney, Murat and Essiz, Selçuk and Daştan, Arif and Balci, Metin and DE LUCCHI, Ottorino and Şahin, Ertan and FABRIS, Fabrizio},
title = {Stereoconvergent Generation of a Contrasteric syn-Bicyclopropylidene (=syn-Cyclopropylidenecyclopropane) by Stille-Like Coupling},
journal = {HELVETICA CHIMICA ACTA},
year = {2013},
volume = {96},
number = {5},
pages = {941--950},
issn = {0018-019X},
doi = {10.1002/hlca.201200291},
url = {https://akademik.atauni.edu.tr/yayinlar/66769-stereoconvergent-generation-of-a-contrasteric-syn-bicyclopropylidene-syn}
}