Tetrahedron: Asymmetry

Highly stereoselective transformation of (1S, 3S)-cis-1, 3-disubstituted tetrahydro-β-carbolines into (1S, 3R)-trans-1, 3-disubstituted tetrahydro-β-carbolines: an …

J Dong, TZ Meng, XX Shi, WH Zou, X Lu

Index: Dong, Jing; Meng, Tian-Zhuo; Shi, Xiao-Xin; Zou, Wen-Hui; Lu, Xia Tetrahedron Asymmetry, 2013 , vol. 24, # 15-16 p. 883 - 893

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Abstract

Abstract An efficient and general method for the highly stereoselective transformation of (1S, 3S)-cis-1, 3-disubstituted 1, 2, 3, 4-tetrahydro-β-carbolines (THBCs) into (1S, 3R)-trans-1, 3- disubstituted THBCs is described. The method contains the following three steps: the enantiomerically pure (1S, 3S)-cis-1, 3-disubstituted THBCs 1 were first converted into (1S, 3S)-cis-1, 2, 3-trisubstituted THBCs 2 by N-1-naphthylmethylation/benzylation;(1S, 3S)-cis ...

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