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For reviews, see
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53549088224
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Dearomatized products of addition to phenyl rings have been observed previously only in less than 10% yield: Prof. A. I. Meyers, personal communication, 2004.
-
Dearomatized products of addition to phenyl rings have been observed previously only in less than 10% yield: Prof. A. I. Meyers, personal communication, 2004.
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23
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9744245274
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Oxazolines 1 and 16 were synthesized by a previously reported method: S. Crosignani, A. C. Young, B. Linclau, Tetrahedron Lett. 2004, 45, 9611.
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Oxazolines 1 and 16 were synthesized by a previously reported method: S. Crosignani, A. C. Young, B. Linclau, Tetrahedron Lett. 2004, 45, 9611.
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25
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0041409652
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DMPU and hexamethylphosphoramide (HMPA) have been shown to promote other reactions involving dearomatizing addition steps, probably by facilitating the formation of ion pairs; see: J. Clayden, F. E. Knowles, C. J. Menet, Synlett 2003, 1701;
-
DMPU and hexamethylphosphoramide (HMPA) have been shown to promote other reactions involving dearomatizing addition steps, probably by facilitating the formation of ion pairs; see: J. Clayden, F. E. Knowles, C. J. Menet, Synlett 2003, 1701;
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26
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0029827163
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[3] but none performed as well as 1.
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[3] but none performed as well as 1.
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28
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53549088492
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CCDC 670194 (3), CCDC 670195 (11), CCDC 670196 (12), CCDC 670197 (18a), and CCDC 670198 (18c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
CCDC 670194 (3), CCDC 670195 (11), CCDC 670196 (12), CCDC 670197 (18a), and CCDC 670198 (18c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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53549123732
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The stereoselectivity of both the dearomatizing addition and the alkylation appears to be greater than 10:1, as no stereoisomeric dearomatized products were observable in the NMR spectrum of the crude reaction mixture. We assume that the configuration of the product arises from coordination of isopropyllithium to the basic nitrogen atom of the oxazoline, followed by 1,4-addition to the 2-position of the p-methoxyphenyl ring from the face anti to the 4-phenyl substituent of the oxazoline ring. Details of the mechanism are still under investigation; however, preliminary attempted trapping experiments suggest that radical intermediates are not involved
-
The stereoselectivity of both the dearomatizing addition and the alkylation appears to be greater than 10:1, as no stereoisomeric dearomatized products were observable in the NMR spectrum of the crude reaction mixture. We assume that the configuration of the product arises from coordination of isopropyllithium to the basic nitrogen atom of the oxazoline, followed by 1,4-addition to the 2-position of the p-methoxyphenyl ring from the face anti to the 4-phenyl substituent of the oxazoline ring. Details of the mechanism are still under investigation; however, preliminary attempted trapping experiments suggest that radical intermediates are not involved.
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0000204167
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B. A. Barner, A. I. Meyers, J. Am. Chem. Soc. 1984, 106, 1865. The oxazolidine intermediates 5 and 9 were formed as single stereoisomers, the configuration of which was not assigned.
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B. A. Barner, A. I. Meyers, J. Am. Chem. Soc. 1984, 106, 1865. The oxazolidine intermediates 5 and 9 were formed as single stereoisomers, the configuration of which was not assigned.
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45
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53549093475
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1H NMR spectrum.
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1H NMR spectrum.
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46
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53549086052
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The configuration of the adducts was assigned by analogy with 3, 18a, and 18c.
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The configuration of the adducts was assigned by analogy with 3, 18a, and 18c.
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