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Wang S, Seto CT. Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide. Org Lett. 2006;8(18):3979-82doi: 10.1021/ol0614525.
Wang, S., & Seto, C. T. (2006). Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide. Organic letters, 8(18), 3979-82. https://doi.org/10.1021/ol0614525
Wang, Sa, and Seto, Christopher T. "Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide." Organic letters vol. 8,18 (2006): 3979-82. doi: https://doi.org/10.1021/ol0614525
Wang S, Seto CT. Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide. Org Lett. 2006 Aug 31;8(18):3979-82. doi: 10.1021/ol0614525. PMID: 16928053.
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Org Lett. 2006 Aug 31;8(18):3979-82. doi: 10.1021/ol0614525.

Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide.

Organic letters

Sa Wang, Christopher T Seto

Affiliations

  1. Department of Chemistry, Brown University, 324 Brook Street Box H, Providence, RI 02912, USA.

PMID: 16928053 DOI: 10.1021/ol0614525

Abstract

Ligand 2a promotes the enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide to yield chiral allylic hydroxylamines. With 0.1 equiv of the ligand, the product is obtained in up to 84% ee, whereas with 1.2 equiv of the ligand, the ee is increased to the 90-95% range with a variety of aliphatic, cyclic, and aromatic vinylzinc reagents. This method was used to synthesize the protected unnatural amino acid N-Cbz-d-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid in three steps from the allylic hydroxylamine.

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