Chiral aziridine-2-carboxylates: versatile precursors for functionalized tetrahydroisoquinoline (THIQ) containing heterocycles

초록

Preparation of functionalized 3,4-dihydroisoquinolines 17a j from (S)-N-methoxy-N-methy1-1-[(R)1-phenylethyl]aziridine-2-carboxamide 4 is an effective route for the synthesis of 3-(hydroxymethyl)1,2,3,4-tetrahydroisoquinolin-4-ols. Stereoselective reduction of the cyclic imines 17a-j resulted in (1S,3S,4R)-4-(rert-butyldimethylsilyl-oxy)-3-1(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2di5ub5tituted-1,2,3,4-tetrahydroisoquinolines and the desilylation of the TBS groups afforded (15,3S,4R)3-(hydroxymethyl)-6,7-dimethoxy-1,2-disubstituted-1,2,3,4-tetrahydroisoquinolin-4-ols 19a i in goodyields. Also, an asymmetric synthesis of novel tetracyclic 3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinolin4-ols 23 and 25 was successfully achieved via Pd-catalyzed N-arylation and C-C coupling reaction. (C) 2011 Elsevier Ltd. All rights reserved.

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