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Issue 1, 2017
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Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit

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Abstract

A pseudo-enantiomeric pair of optically switchable helicenes containing a catalytic 4-N-methylaminopyridine (MAP) bottom unit and a C2-symmetric, (10R,11R)-dimethoxymethyl-dibenzosuberane top template was synthesized. They underwent complementary photoswitching at 290 nm (P/M′, <1/>99) and 340 nm (P/M′, 91/9) and unidirectional thermo-rotation at 130 °C (P/M′, >99/<1). They were utilized to catalyze enantiodivergent Steglich rearrangement of O- to C-carboxylazlactones, with formation of either enantiomer with up to 91% ee (R) and 94% ee (S), respectively.

Graphical abstract: Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit

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Publication details

The article was received on 16 Jun 2016, accepted on 23 Aug 2016 and first published on 25 Aug 2016


Article type: Edge Article
DOI: 10.1039/C6SC02646J
Citation: Chem. Sci., 2017,8, 524-529
  • Open access: Creative Commons BY-NC license
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    Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit

    C. Chen, C. Tsai, P. Tsou, G. Huang and C. Yu, Chem. Sci., 2017, 8, 524
    DOI: 10.1039/C6SC02646J

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