Journal of the American Chemical Society
Article
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(23) For a computational analysis and comparison of C−H insertion
processes by Rh- and Cu-carbenoids, see: (a) Nakamura, E.; Yoshikai,
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(24) Substrate 14g (R1 = phenyl) was also synthesized. Subjection of
this compound to the standard reaction conditions provided the
corresponding C−H insertion product; no cyclopropanation products
were detected. This entry was omitted from Table 2 because of the
difficulties in obtaining analytically pure quantities of the C−H
insertion product. For examples of inter- and intramolecular C−H
insertion of donor−acceptor diazo compounds, see: (a) Taber, D. F.;
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(26) For similar substituent effects observed with the terminal
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(28) Cyclopropanation of electron deficient alkenes via a concerted
cycloaddition mechanism is typically disfavored with electrophilic
rhodium-carbenoids; however, several other metals catalyze these
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(30) Lindsay, V. N. G.; Fiset, D.; Gritsch, P. J.; Azzi, S.; Charette, A.
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(31) The relative stereochemistry of the newly formed methine could
not be definitively assigned by NOE experiments; however, related
examples of stereospecific SN2′ reactions of cuprates would suggest the
stereoisomer of 26 as shown. See: (a) Casey, C. P.; Cesa, M. C. J. Am.
Chem. Soc. 1979, 101, 4236. (b) Corey, E. J.; Fuchs, P. L. J. Am. Chem.
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(32) The relative stereochemistry was determined by NOE analysis
(see Supporting Information) and is consistent with previously
reported SN2 ring-opening of activated cyclopropanes, see reference
31.
(17) Doyle, M. P.; Shanklin, M. S.; Oon, S. M.; Pho, H. Q.;
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(18) Buchner reactions of A−A diazo substrates containing three
atom linkers: (a) Park, C. P.; Nagle, A.; Yoon, C. H.; Chen, C. L.;
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(19) On the basis of our previous studies, Heinrich et al. recently
reported that an α-diazo-β-ketonitrile substrate analogous to 7 but
lacking the isodihydrofuran ring undergoes cyclopropanation with
Rh2(OAc)4 to afford a stable norcaradiene. Heinrich, N.; Banwell, M.
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G
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