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Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides.

Publication ,  Journal Article
Daniel, PE; Weber, AE; Malcolmson, SJ
Published in: Organic letters
July 2017

We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.

Duke Scholars

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

July 2017

Volume

19

Issue

13

Start / End Page

3490 / 3493

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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ICMJE
MLA
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Daniel, P. E., Weber, A. E., & Malcolmson, S. J. (2017). Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides. Organic Letters, 19(13), 3490–3493. https://doi.org/10.1021/acs.orglett.7b01471
Daniel, Paige E., Alexandria E. Weber, and Steven J. Malcolmson. “Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides.Organic Letters 19, no. 13 (July 2017): 3490–93. https://doi.org/10.1021/acs.orglett.7b01471.
Daniel PE, Weber AE, Malcolmson SJ. Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides. Organic letters. 2017 Jul;19(13):3490–3.
Daniel, Paige E., et al. “Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides.Organic Letters, vol. 19, no. 13, July 2017, pp. 3490–93. Epmc, doi:10.1021/acs.orglett.7b01471.
Daniel PE, Weber AE, Malcolmson SJ. Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides. Organic letters. 2017 Jul;19(13):3490–3493.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

July 2017

Volume

19

Issue

13

Start / End Page

3490 / 3493

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences