Journal
TETRAHEDRON LETTERS
Volume 58, Issue 2, Pages 129-133Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.11.110
Keywords
Asymmetric synthesis; Diastereoselectivity; Acid catalysis; Oxa-Pictet-Spengler; Tetrahydropyran[3,4-b]indole
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Funding
- National Natural Science Foundation of China [21072087]
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We successfully explored for the first time that trifluoroacetic acid (TFA) can effectively catalyze the oxaPictet-Spengler reaction of secondary tryptophols and acetals to synthesize 1,3-disubstituted 1,3,4,9-tetrahydropyrano[3,4-b]indoles in high yield (up to >99%) and diastereoselectivity (>20:1). The secondary tryptophols were synthesized from indole-3-acetic acid. The one-pot synthesis of tetrahydropyrano[3,4blindoles was successfully developed from secondary tryptophols and in situ prepared acetals from aldehydes and trimethylorthoformate and thus the cost-efficiency of the protocol was effectively enhanced. Finally, the catalytic asymmetric synthesis of the 1,3-disubstituted tetrahydropyrano[3,4-b]indole was also demonstrated after enantioselective achievement of highly enantiopure secondary tryptophols. (C) 2016 Elsevier Ltd. All rights reserved.
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