Asymmetric Synthesis of α-Allyl-α-Aryl α-Amino Acids by Tandem Alkylation/π-Allylation of α-Iminoesters
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作者:
Curto, John M.
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Univ Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USA
Curto, John M.
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Dickstein, Joshua S.
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Univ Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USA
Dickstein, Joshua S.
[1
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Berritt, Simon
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Univ Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USA
Berritt, Simon
[1
]
Kozlowski, Marisa C.
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Univ Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USA
Kozlowski, Marisa C.
[1
]
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[1] Univ Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USA
The first asymmetric synthesis of alpha-allyl-alpha-aryl alpha-amino acids by means of a three-component coupling of alpha-iminoesters, Grignard reagents, and cinnamyl acetate is reported. Notably, the enolate from the tandem process provides a much higher level of reactivity and selectivity than the same enolate generated via direct deprotonation, presumably due to differences in the solvation/aggregation state. A novel method for removal of a homoallylic amine protecting group delivers the free amine congeners. The alpha-allyl group offers a means to generate further valuable alpha-amino acid structures as exemplified by ring closing metathesis to generate a higher ring homologue of alpha-aryl-proline.