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Syn-Selective anti-Markovnikov Intramolecular Hydroamination

J. Hartwig, Atsushi Takemiya

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Abstract

Significance Using a Rh(I)/DPPB catalyst system, aminoolefins undergo a remarkably selective anti-Markovnikov hydroamination reaction to generate 3-arylpiperidines in good yields. When the aminoolefin is appropriately substituted (R ≠ H), products are obtained with high degrees of syn -selectivity; presumably due to equatorial placement of the substituents in a chair-like transition state. The N -methyl substituent is necessary for the reaction to proceed; however, this group can be easily cleaved (see scheme).

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Significance Using a Rh(I)/DPPB catalyst system, aminoolefins undergo a remarkably selective anti-Markovnikov hydroamination reaction to generate 3-arylpiperidines in good yields. When the aminoolefin is appropriately substituted (R ≠ H), products are obtained with high degrees of syn -selectivity; presumably due to equatorial placement of the substituents in a chair-like transition state. The N -methyl substituent is necessary for the reaction to proceed; however, this group can be easily cleaved (see scheme).

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Available abstract

Significance Using a Rh(I)/DPPB catalyst system, aminoolefins undergo a remarkably selective anti-Markovnikov hydroamination reaction to generate 3-arylpiperidines in good yields. When the aminoolefin is appropriately substituted (R ≠ H), products are obtained with high degrees of syn -selectivity; presumably due to equatorial placement of the substituents in a chair-like transition state. The N -methyl substituent is necessary for the reaction to proceed; however, this group can be easily cleaved (see scheme).

Key concepts: Hydroamination, Markovnikov's rule, Chemistry, Intramolecular force, Substituent, Selectivity, Catalysis, Medicinal chemistry

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