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Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes.

Publication ,  Journal Article
Adamson, NJ; Park, S; Zhou, P; Nguyen, AL; Malcolmson, SJ
Published in: Organic letters
March 2020

We report the enantioselective formation of quaternary stereogenic centers by the intermolecular addition of malononitrile, an acyl anion equivalent, and related pronucleophiles to several 1,3-disubstituted acyclic 1,3-dienes in the presence of a Pd-PHOX catalyst. Products are obtained in up to 88% yield and 99:1 er and in most cases are formed as a single regioisomer. The products' malononitrile unit undergoes oxidative functionalization to afford β,γ-unsaturated carbonyls bearing internal olefins and α-quaternary stereogenic centers.

Duke Scholars

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2020

Volume

22

Issue

5

Start / End Page

2032 / 2037

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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MLA
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Adamson, N. J., Park, S., Zhou, P., Nguyen, A. L., & Malcolmson, S. J. (2020). Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes. Organic Letters, 22(5), 2032–2037. https://doi.org/10.1021/acs.orglett.0c00412
Adamson, Nathan J., Sangjune Park, Pengfei Zhou, Andrew L. Nguyen, and Steven J. Malcolmson. “Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes.Organic Letters 22, no. 5 (March 2020): 2032–37. https://doi.org/10.1021/acs.orglett.0c00412.
Adamson NJ, Park S, Zhou P, Nguyen AL, Malcolmson SJ. Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes. Organic letters. 2020 Mar;22(5):2032–7.
Adamson, Nathan J., et al. “Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes.Organic Letters, vol. 22, no. 5, Mar. 2020, pp. 2032–37. Epmc, doi:10.1021/acs.orglett.0c00412.
Adamson NJ, Park S, Zhou P, Nguyen AL, Malcolmson SJ. Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes. Organic letters. 2020 Mar;22(5):2032–2037.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2020

Volume

22

Issue

5

Start / End Page

2032 / 2037

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences