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85064658013
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Carbamates la-c were prepared from l-substituted-2, 4-dienylamine (tricarbonyl)iron complexes4 by a two-step sequence of protection of the amino group and decomplexation of the Fe(CO)3 group, or vice versa. Id was obtained from a known compound, 1, 1-dimethylethyl 4-formyl-2, 2-dimethyl-3-oxazolidinecarboxylate (Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361), in 7 steps [(1) CH2CHCH2PPh3Br, KN(TMS)2; (2) p-TsOH, MeOH; (3) MOMC1, (i-Pr)2NEt; (4) BnBr, NaH; (5) CF3C02H; (6) MeOCOCl, K2C03; (7) 3N HC1, THF]
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Carbamates la-c were prepared from l-substituted-2, 4-dienylamine (tricarbonyl)iron complexes4 by a two-step sequence of protection of the amino group and decomplexation of the Fe(CO)3 group, or vice versa. Id was obtained from a known compound, 1, 1-dimethylethyl 4-formyl-2, 2-dimethyl-3-oxazolidinecarboxylate (Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361), in 7 steps [(1) CH2CHCH2PPh3Br, KN(TMS)2; (2) p-TsOH, MeOH; (3) MOMC1, (i-Pr)2NEt; (4) BnBr, NaH; (5) CF3C02H; (6) MeOCOCl, K2C03; (7) 3N HC1, THF].
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27
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85064649522
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Reaction with other iodonium reagents, such as N-iodosuccinimide and iodonium dicollidine perchlorate, resulted in low yield (10- 20%) and no stereoselectivity (2/3 = 1/1- 3/2)
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Reaction with other iodonium reagents, such as N-iodosuccinimide and iodonium dicollidine perchlorate, resulted in low yield (10- 20%) and no stereoselectivity (2/3 = 1/1- 3/2).
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28
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85064693795
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The addition of KI to the reaction mixture dramatically promoted both the reaction rate and the chemical yield without any loss of stereoselectivity
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The addition of KI to the reaction mixture dramatically promoted both the reaction rate and the chemical yield without any loss of stereoselectivity.
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29
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85064592723
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The relative stereochemistry of 2a-d and 3a-d was determined by NOE measurements of C4-H and vinylic proton (Cl'-H) or C4-H and C5-H, respectively
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The relative stereochemistry of 2a-d and 3a-d was determined by NOE measurements of C4-H and vinylic proton (Cl'-H) or C4-H and C5-H, respectively.
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30
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0021181831
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Kobayashi, S.; Isobe, T.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079.
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Kobayashi, S.1
Isobe, T.2
Ohno, M.3
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