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Nakamura S, Tanaka M, Taniguchi T, et al. Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions. Org Lett. 2003;5(12):2087-90doi: 10.1021/ol034526a.
Nakamura, S., Tanaka, M., Taniguchi, T., Uchiyama, M., & Ohwada, T. (2003). Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions. Organic letters, 5(12), 2087-90. https://doi.org/10.1021/ol034526a
Nakamura, Satoshi, et al. "Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions." Organic letters vol. 5,12 (2003): 2087-90. doi: https://doi.org/10.1021/ol034526a
Nakamura S, Tanaka M, Taniguchi T, Uchiyama M, Ohwada T. Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions. Org Lett. 2003 Jun 12;5(12):2087-90. doi: 10.1021/ol034526a. PMID: 12790535.
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Org Lett. 2003 Jun 12;5(12):2087-90. doi: 10.1021/ol034526a.

Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions.

Organic letters

Satoshi Nakamura, Masaru Tanaka, Tooru Taniguchi, Masanobu Uchiyama, Tomohiko Ohwada

Affiliations

  1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 12790535 DOI: 10.1021/ol034526a

Abstract

[reaction: see text] High stereoselectivities were found in a wide range of superacid-catalyzed Pictet-Spengler cyclization reactions. Particularly in the cases of 2-alkyl-N-benzylidene-2-phenethylamines, an enhanced stereoselectivity was observed under the superacid conditions as compared with the corresponding weak acid (TFA)-catalyzed (monocationic) cyclization reaction of the N-benzylidene-2-(3',4'-dimethoxy)phenethylamines that bear electron-donating groups on the cyclizing aromatic ring. The computational study also supported the energetic favorability of the cyclization of the N,N-diprotonated imine and revealed a significantly early transition-state structure.

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