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Yamanaka M, Sakata K, Yoshioka K, et al. Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study. J Org Chem. 2016;82(1):541-548doi: 10.1021/acs.joc.6b02572.
Yamanaka, M., Sakata, K., Yoshioka, K., Uraguchi, D., & Ooi, T. (2017). Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study. The Journal of organic chemistry, 82(1), 541-548. https://doi.org/10.1021/acs.joc.6b02572
Yamanaka, Masahiro, et al. "Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study." The Journal of organic chemistry vol. 82,1 (2017): 541-548. doi: https://doi.org/10.1021/acs.joc.6b02572
Yamanaka M, Sakata K, Yoshioka K, Uraguchi D, Ooi T. Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study. J Org Chem. 2017 Jan 06;82(1):541-548. doi: 10.1021/acs.joc.6b02572. Epub 2016 Dec 20. PMID: 27997163.
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J Org Chem. 2017 Jan 06;82(1):541-548. doi: 10.1021/acs.joc.6b02572. Epub 2016 Dec 20.

Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study.

The Journal of organic chemistry

Masahiro Yamanaka, Ken Sakata, Ken Yoshioka, Daisuke Uraguchi, Takashi Ooi

Affiliations

  1. Department of Chemistry and Research Center for Smart Molecules, Faculty of Science, Rikkyo University , 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan.
  2. Faculty of Pharmaceutical Sciences, Hoshi University , Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.
  3. Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University , Nagoya 464-8602, Japan.
  4. CREST, Japan Science and Technology Agency (JST), Nagoya University , Nagoya 464-8602, Japan.

PMID: 27997163 DOI: 10.1021/acs.joc.6b02572

Abstract

Chiral P-spiro triaminoiminophosphorane (1) was developed to promote the highly regio-, diastereo-, and enantioselective 1,6- and 1,8-additions of azlactones (2·H) to dienyl and trienyl N-acylpyrroles (3 and 4). DFT calculations enabled us to gain deep insight into the whole reaction mechanism as well as the origin of the high regio- and stereoselectivities. The present reaction consists of three steps: (1) formation of the phosphonium-enolate ion-pair complex by deprotonation of 2·H with 1, (2) C-C bond formation of 2 with 3 and 4, and (3) protonation of the resulting enolate anion. The C-C bond formation is irreversible, and the rate- and stereodetermining step. The C

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