Asymmetric Synthesis of Tetrahydro-β-carboline Alkaloids Employing­ Ellman’s Chiral Auxiliary

Abstract

A stereoselective synthesis of tetrahydro-β-carboline alkaloids has been accomplished using Ellman’s sulfinamide as a chiral source. This is the first report on the synthesis of chiral tetrahydro-β-carboline natural products using tert-butanesulfinamide through haloamide cyclization. Similarly, the synthesis of an indolizino[8,7-b]indole alkaloid, (–)-harmicine, has been achieved by means of allylation of an N-sulfinylimine, hydroboration, and S_N2 substitution.

Keywords

asymmetric synthesis - chiral auxiliaries - Grignard reaction - imines - organometallic reagents

• References and Notes

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