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Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.

Publication ,  Journal Article
Zhang, Z; Bender, CF; Widenhoefer, RA
Published in: Organic letters
July 2007

Treatment of the N-4,5-hexadienyl carbamate 2a with a catalytic 1:2 mixture of [(S)-1]Au2Cl2 [(S)-1 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgClO4 in m-xylene at -40 degrees C for 24 h led to isolation of 2-vinylpyrrolidine 3a in 97% yield with 81% ee. Gold(I)-catalyzed enantioselective hydroamination was effective for a number of carbamate groups and tolerated terminal disubstitutution of the allenyl moiety.

Duke Scholars

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

July 2007

Volume

9

Issue

15

Start / End Page

2887 / 2889

Related Subject Headings

  • Stereoisomerism
  • Organic Chemistry
  • Gold
  • Catalysis
  • Carbamates
  • Amination
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

APA
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ICMJE
MLA
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Zhang, Z., Bender, C. F., & Widenhoefer, R. A. (2007). Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates. Organic Letters, 9(15), 2887–2889. https://doi.org/10.1021/ol071108n
Zhang, Zhibin, Christopher F. Bender, and Ross A. Widenhoefer. “Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.Organic Letters 9, no. 15 (July 2007): 2887–89. https://doi.org/10.1021/ol071108n.
Zhang Z, Bender CF, Widenhoefer RA. Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates. Organic letters. 2007 Jul;9(15):2887–9.
Zhang, Zhibin, et al. “Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.Organic Letters, vol. 9, no. 15, July 2007, pp. 2887–89. Epmc, doi:10.1021/ol071108n.
Zhang Z, Bender CF, Widenhoefer RA. Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates. Organic letters. 2007 Jul;9(15):2887–2889.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

July 2007

Volume

9

Issue

15

Start / End Page

2887 / 2889

Related Subject Headings

  • Stereoisomerism
  • Organic Chemistry
  • Gold
  • Catalysis
  • Carbamates
  • Amination
  • 34 Chemical sciences
  • 03 Chemical Sciences