Synthesis of Chiral 1-Substituted Tetrahydroisoquinolines by the Intramolecular 1, 3-Chirality Transfer Reaction Catalyzed by Bi (OTf) 3

…, R Abe, M Matsuda, J Uenishi

文献索引：Kawai, Nobuyuki; Abe, Ryuzou; Matsuda, Mika; Uenishi, Jun'Ichi Journal of Organic Chemistry, 2011 , vol. 76, # 7 p. 2102 - 2114

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被引用次数: 25

摘要

The intramolecular 1, 3-chirality transfer reaction of chiral amino alcohols 1 with 99% ee was developed to construct chiral 1-substituted tetrahydroisoquinoline 2. Bi (OTf) 3 (10 mol%)- catalyzed cyclization of 1 (R= H) afforded (S)-1-(E)-propenyl tetrahydroisoquinoline 2 (R= H) in 83% yield with a ratio of 98: 2. The stereochemistry at the newly formed chiral center was produced by a syn SN2′-type process. In this reaction, the substituent on the benzene ...